


As Far As You Want

by Isis_McGee



Series: How Far 'verse [1]
Category: Supernatural
Genre: Begging, Dirty Talk, Dom/sub, Double Penetration, Handcuffs, Light BDSM, Light Bondage, Multi, Oral Sex, Pegging, Threesome - F/M/M, Wax Play
Language: English
Status: Completed
Published: 2015-02-28
Updated: 2015-02-28
Packaged: 2018-03-15 13:44:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 27,777
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3449333
Author URL: https://archiveofourown.org/users/Isis_McGee/pseuds/Isis_McGee
Summary: <blockquote class="userstuff">
              <p>Or: How to End Up in an Incestuous Polyamorous Relationship and Like It</p><p>Sam and Jess were just looking for a nice guy to invite into their bed; Sam had no idea Jess would end up choosing his brother and he had even less of an idea that somehow the three of them would work it out.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Special thanks to my beta, acehardy3, who did a great job in a short time, and my artist, deadlyfurniture, who dealt with my procrastination so well and created something great you can see in chapter 3.
> 
> Just as a reminder, I'd like to be clear that this is solely my interpretation of how these characters may navigate a BDSM type relationship. Nothing depicted in this fic is meant to represent BDSM as a whole or comment on it as a choice.

Sam couldn’t stop staring at the dildo in front of his eyes. It was bright pink and stuck to the shelf and when he accidentally knocked into the display a little when someone passed by him, it wiggled, the light catching it just right to show that it shimmered. It was also huge‒ it wasn’t too bad in length, but in width. Sam couldn’t imagine anyone comfortably having it inside them, even if the color didn’t put them off. He tried to force his eyes elsewhere, but he couldn’t until Jess came and snapped him out of his hypnosis.

“I don’t think that would qualify as safe for anal play, Sam. Not any that we’d be doing any time soon.”

“Oh, God, no. I know that,” Sam laughed. “It was just right there. I couldn’t look away.”

Jess laughed back at him, her smile widening into it and her teeth showing. Their hands linked and locked between them as they’d done a thousand times when she leaned up to give him a quick kiss.

“We don’t have to do this, you know. I mean, we can just stay for this workshop, find some toys we might want to try. If you’re not backing out‒”

“Nice,” Sam interrupted with a smile.

“Don’t point out my dumb puns,” Jess fake chastised. “If you really want to try some back door stuff other than a finger during a blow job, I think our best bet right now would be some small beads. Or I saw some where the beads got bigger down the string and that could be fun.”

“You’re awfully enthusiastic about this,”

“I am. You’ve got such a cute butt; I just wanna play with it.” Sam laughed. “But only if you still want me to.”

“I’m still into the idea, yeah, Jess,” Sam said. He paused and made sure he had Jess’ attention before he went on. “And just so you know, I’m still into this other idea too. I know you want this and I want to do that for you. And I know you’re going to say that you don’t want me doing it just for you. I’m not.”

Jess squeezed Sam’s hand and the smile she gave him was soft and full of love. “How did I manage to get such a good guy, huh?”

“I’m not that good,” Sam said, shrugging one shoulder. He glanced around at their surroundings as he did it, seeing that the shelf opposite the dildo display was full of different types of lubricant and the one next to that was full of books, both erotica and manuals. He’d just noticed the rows of multicolored ropes and the selection of handcuffs he was sure he could probably slip easily enough when Jess swatted him lightly on the arm.

“I mean it. I’m glad we’re so honest with each other.”

If Jess saw the wince Sam tried to cover up at that, she didn’t say anything to him about it. She had half turned away from him to examine the small vibrator on the shelf in front of her and Sam hoped she’d simply missed it.

“Then if we’re being honest, you don’t need another vibrator,” Sam joked.

“Hey, I was looking for you,” Jess shot back. “If we wanted to skip the beads, maybe we could find you a prostate massager. You’d probably‒”

“Are we still talking about this to avoid talking about finding another guy you want to bring into our sex life?”

Jess looked down. “Maybe.”

“Are you nervous about it?”

She turned, putting her back to the wall of shelves they’d been half-looking at and leaning against the lip of the counter in front of one. Jess tilted her head to look up at Sam and she looked almost embarrassed.

“How do you even approach someone about this? And so far, it’s seemed like everyone wandering in here has been part of a couple. And I’ve done the girl thing and it wasn’t really doing anything for me, so I don’t know that a foursome would be my thing. I mean, I suppose I could try it again since it’d be different, but‒”

“Jess, sweetheart, you’re rambling,” Sam said; she shot him a look at the term of endearment and Sam held his hands up in a motion of surrender.

“Aren’t you nervous?”

“I don’t have to choose him. You get to choose him and I just have to approve.”

“You’re not worried he’ll take one look at you and get scared off because you’re a giant and it’s obvious your dick could possibly wound a guy? And definitely bruise his ego?”

Sam screwed up his face in bafflement and his hands came up again, this time in confusion. He shook his head as he spoke. “First, that’s ridiculous. And second, no, I hadn’t been worried about me putting off the guy until you brought it up.”

Sam’s voice had gone slightly higher during that last part and Jess smiled apologetically.

“I’m sorry, that was dumb. We’ll find a guy we both want and who wants both of us and it’ll be fine. It’ll be good. We’re just psyching ourselves out about this.”

“You’re psyching us out about this,” Sam corrected. “Sorry,” he laughed but didn’t retract the statement when Jess glared at him. He couldn’t mention to her that this was far from the scariest thing he’d ever dealt with and somehow he felt fairly calm. The worst thing that could happen was that they wouldn’t find someone, or they would find someone and it didn’t work out; Sam wasn’t exactly worried about defending themselves from psychos. “Look, I’m going to go sit down in the back room and look like I’m just waiting for this lecture to start. You stay up here and wait to see if a guy catches your eye. If he does, just talk to him. But he’ll probably talk to you first, Jess.”

“So what, I should just wait to get hit on?” Jess shook her head a little and her curls bounced. Sam snorted.

“That’s not what I said.”

Jess sighed. “I know.” Her mouth quirked up into a half smile. She waved a hand at Sam, “Go. Let me hit on other men.”

Sam smiled back and leaned down to kiss Jess. She snaked a hand around to pinch his butt as he did and he let out a short yelp for the benefit of how she grinned with her bottom lip caught in her teeth whenever he made the sound. He shot her a cheesy, double thumbs up before he headed toward the back room. It was separated from the shop area by a red velvet curtain that looked like it belonged on a stage and kept the merchandise blocked off from anyone who came in the back door. Along with the lectures and workshops such as the one that night on safe anal play, sometimes the Stanford professors who worked with Human Sexuality organized events that could entail people under the age of 18; he liked that for that reason there was a separation between what he would be doing and what Jess was doing.

Sam sat down in a seat one from the end of an aisle and avoided eye contact with anyone as much as possible as he picked up the program from the chair next to him and pretended to read as though he wasn’t thinking about Jess on the other side of the curtain and the prospect of sleeping with her and another man both.

***

While Sam was keeping himself from twisting the lecture program to bits in his hand, Jess was trying to pretend to be looking at books while really glancing at every single person she heard enter the store. There’d actually been quite a few people, but most seemed to be couples who were there for the workshop. Jess was fairly certain she recognized her freshman English teacher’s assistant and her partner, but she tried not to concentrate on anyone else’s features very long after that. She didn’t want to know about any of her professor’s sex lives‒ although she wasn’t naïve enough to think they didn’t have them‒ and more importantly, she didn’t need any of them to know anything about her sex life by recognizing her; she wanted this to be nice and anonymous. She’d hate for either her or Sam to accidentally run into this guy in a class or a club or anything. With the best luck possible, a tall, gorgeous, bisexual engineering major from Santa Clara University would walk through the door and be looking for a couple to have a threesome with; however, Jess didn’t hold her breath for that to happen.

The first guy who came through the door on his own was immediately a no go. Jess didn’t want to be shallow, but the man was far older than she’d even considered and a bit on the paunchy side. He wasn’t completely unattractive, but there was no way he’d look attractive if she stood him next to Sam and he would know that. Jess pictured how that encounter could go and shook her head a little. He wasn’t an option. She went back to pretend thumbing through a book that she actually had no idea what it was about.

It was another almost ten minutes, so close to the lecture’s start time that Jess thought she might have to give up, before another single man came in. Jess glanced his way and immediately did a double take. She couldn’t help herself; he was absolutely beautiful. He wore an old leather jacket‒ brown, which made him seem less like he was trying too hard‒ over a black t-shirt and maroon button down. But Jess was surprised that she even noticed he was wearing clothes; she couldn’t seem to tear her eyes away from his face. She knew she was standing there with the book completely closed and that she was staring, but she couldn’t stop. His lips were full and pink and pouty enough that she thought she might be jealous. Jess marveled at his cheekbones. He was only a little taller than her if that so when he turned and saw her staring, she could see his green eyes go wide, then crinkle a little as he smiled. Jess felt herself blush.

He didn’t approach her right away and Jess kept stealing glances at him as he looked around, clearly on the hunt for something, lips pursing up in concentration. She could feel his eyes back on her and when she heard his footsteps a nervous little rush went through her. The possibility that this wouldn’t work had flown from her mind at some point and she remembered what it was like flirting with boys at frat parties and with the bouncers who didn’t want to believe her fake ID and she was confident until the guy spoke up.

“Excuse me, you wouldn’t happen to work here would you?”

“I’m sorry?” Jess asked, finally looking up at him. She hadn’t expected that at all. His face split into a small grin. She shook her head a little and processed what he said. “No, I don’t work here.”

“That’s too bad, I was hoping you might be able to help me find something.”

Jess raised an eyebrow at him skeptically. There was something in the tone of his voice that told her there was a line coming. She couldn’t tell if she wanted there to be one or not.

“I might be able to help you any way,” Jess told him with a small smile of her own, dropping the eyebrow she’d raised.

“I was looking for a girl, tall, blond, killer legs, pretty blue eyes, cute little mole on her forehead. I can’t quite remember her name though.”

At any other time, for any other guy, Jess would have rolled her eyes and walked away. As it was, she settled for rolling her eyes. The guy was still smirking.

“Does that sort of thing work for you a lot?” Jess asked, unable to help herself. The guy grinned.

“What do you think?”

“I think you’re probably one of those pretty boys who gets away with a lot of shit with women,” Jess said. She winced at how harsh she sounded. This was not how she wanted this encounter to go. But he laughed.

“You’re not wrong. Sorry if I offended, I can‒” he made a move to turn away and leave Jess alone and she stopped him with a hand on his forearm.

“My name’s Jess,” she told him. She looked at him expectantly.

“Dean.”

“Well, Dean, what’d you really come in here for?”

“Condoms. Haven’t seen a drug store or a gas station in miles. What’d you come in here for?” Dean tilted his head and read off the title of the book Jess was holding “Desperately needed ‘The Complete Guide to Cunnilingus’ on a Thursday night? Boyfriend that bad that he needs a manual?”  

Jess could hear the leer in his voice and she sort of wanted to whack him across the head with the book, but she shoved it back into its slot on the shelf instead. “No, I’m here for the workshop. With my boyfriend,” Jess used her thumb to gesture toward the curtain behind her then added, “Who definitely does _not_ need that book.”

Dean put a mild look on his face as though it acted as an apology before it turned into something else. “Does this boyfriend know you’re out here talking to other men?”

“Yes,” Jess told him, making sure to keep eye contact. She saw his eyebrows rocket up and she couldn’t help but smirk. She didn’t go on and it was clear that Dean was dying for her to.

“Okay, I’ll bite. What’s that about?”

Cocking her head a little and biting her lip, Jess considered how to explain. She dove head first. “How do you feel about threesomes?”

Dean blinked a little, his forehead still wrinkled by his raised eyebrows and then he split into a grin. “Well, I’d feel better about them if you had a girlfriend you were joining back there, but I’m for them either way.” He sounded smug and Jess didn’t particularly like it, but she still felt a little warm when she watched him lick his lips.

“Okay. Good.”

“Okay,” Dean repeated. “You wanna run along and get your boyfriend there or…?”

Jess shook her head. “No. We’re really here for this lecture too. You can come sit in‒”

“Not a lecture kind of guy.”

“Meet us at the bar down the street in an hour then. Harrison’s.”

“Alright.” Dean nodded and his eyes searched around the room again. Jess could see when he spotted what he’d been looking for and he made a move towards her. She stepped back a little and Dean smirked. “Relax,” he told her and pulled his arm back from where he’d reached behind her. He had a fist full of condoms in a rainbow of foil wrappers and a myriad of scripts that proclaimed how they were ribbed and lubricated. “Definitely need these now.”

“You know that we’re still in charge of this, right? If we get in there and my boyfriend takes a look at you and says no, it’s a no. If I change my mind‒”

Dean didn’t let Jess finish. He was already nodding. “I’m the guest star, I get it. Not my first rodeo. You run the show.”

The tiniest thrill ran through Jess at his words, but more so she was flooded with relief. This was almost too perfect and suddenly‒

“You’re not a hooker, are you?” Dean looked so taken aback that Jess started to giggle, throwing a hand up in front of her mouth to cover the fact that it turned into nervous laughter in no time. His surprise morphed into offense and Jess shook her head. “I’m sorry, it’s just that this suddenly seemed too easy.”

Dean shook his head and Jess continued to try to get a hold of her laughter. He shoved the condoms he had still been holding into his pocket and slipped out his wallet. Jess was still giggling when he stepped away from her towards the counter, threw some money down onto it and stepped towards the door.

“Not a hooker, but I’m gonna expect you to get my bar tab since I’ll be waiting,” he said with a wink and then he was gone.

Jess finally stopped giggling‒ _nerves_ ‒ and thought that that had gone well. She slipped past the curtain, hoping she wasn’t causing a scene by entering after the lecture had started. She moved the programs piled on the seat next to Sam and sat. He looked over at her with a question written clear on his face and Jess smiled. She leaned over and whispered that “he’s gorgeous and meeting us at Harrison’s after. Will you be mad at me if I want to sit on his face?”

Jess kissed Sam’s cheek when he shifted in his seat in a way that told her he wouldn’t be mad at all.

***

 

Dean was two beers in and a hundred bucks richer by the time he looked at the clock over the pool table and saw that he should start keeping an eye out for Jess. He’d meant to be in Palo Alto to check in on Sam, try to pick up some co-ed willing to let him spend the night to save the bogus credit card charge for a motel, but honestly, John had left two weeks ago with no indication of when he was going to come back and Dean intended to use the time away to his advantage every way possible. He wouldn’t feel guilty for having fun with a bombshell of a girl and her boyfriend. Besides, John would call and tell him where he needed Dean to be; he’d been the one to send Dean to a hunt out near Kerby, Oregon. It had seemed a waste to be that far out on the coast and not make sure his brother was alright at Stanford‒ he’d driven farther for less.

“Did you shark me?” Dean’s pool opponent asked. The game had been finished for a good five minutes and Dean was just practicing shots since the bar was relatively empty.

“You’re the one who asked me to play, who put the money down, man,” Dean shrugged. The other man was obviously drunk, which Dean guessed was a normal state for him. He seemed harmless though, especially for Dean.

“Oh, right,” he muttered. Dean tried not to laugh.

“Come on, buddy,” Dean said, clapping the man on the back. He lead him to a bar stool and sat him down. “Let’s get you some pretzels.” When the bartender came by, Dean mouthed ‘water’ and left the man to her care. He then proceeded to find a table as far away as possible from the man, which was a high one tucked into the corner.

Dean took a pull from his beer bottle and pulled out his phone to make sure he didn’t have any new messages while he waited. The last thing he’d gotten was the text from John that gave him the coordinates to the hunt in Kerby, so he scrolled through his contacts until he was toying with the idea of calling Sam. He hadn’t talked to the kid in two years, but it felt like most of that had been because John was constantly around.

If this Jess girl and her boyfriend didn’t show up, he could maybe convince Sam to come out and get a beer; he did miss him, even if he didn’t ever do anything to indicate it, even if he was still a little pissed at Sam for leaving in the first place. His thumb was hovering over the button to send Sam a text when he heard the door to the bar open and Dean watched his brother walk in and scan the bar until his eyes fell on Dean.

“What the hell are you doing here?” Sam asked as he approached the table. He sounded pissed and confused and the former was of more interest to Dean.

“Drinking a beer, obviously. Hello to you too, Sammy.”

“What the hell are you doing here in Stanford, Dean? There can’t be a hunt here.” Dean could see Sam’s fist clenching up.

“Why? You been taking care of things? You sure there’s no hunt here? Going after shit by yourself?”

“No, god, no. Of course not,” Sam shook his head. “But I read the paper. I’m an informed person and there’s nothing weird going on around Stanford. So again, why are you here?”

The steam ran out of Dean’s anger at Sam’s tone. “Sit down and have a beer with me.”

“You came all the way out to Stanford to have a beer with me? And you didn’t call?”

“Don’t be a smartass, Sam. There was a hunt in Oregon, thought I’d come down. And if I’d called, you wouldn’t have picked up.”

“You don’t know that‒”

“Just sit down, man.”

Sam glared but he did pull the stool out from the table and sit half-way onto it. He looked ready to bolt at any moment and Dean raised an eyebrow at him. Sam just shrugged, then looked around, his eyes landing on the only other single man in the place other than the drunk Dean had dropped off at the bar. Dean saw Sam’s brow lower in confusion and his nose wrinkle in a little disgust.

“What? Recognize that guy from some frat boy hazing you went through?”

Sam scoffed. “What? No, I just‒”

But whatever he was just was interrupted by the way relief spread across his face when the door of the bar opened and a tall blonde walked in. Dean recognized her as Jess, but he was a little confused as to why Sam looked so happy to see her. He also wondered where exactly this boyfriend of hers was for about two seconds until‒

“Oh, you’ve got to be shitting me,” he sighed. “Please tell me that’s not your girlfriend.”

Sam turned to look at Dean puzzled, then his expression fell into terrible realization. No trace of his previous smile was there and the color drained from his face for a moment before everything seemed to catch up with him and red spots appeared high on his cheeks the way they always used to when he got embarrassed as a kid. Dean couldn’t help but crack a smirk at that and it made Sam’s cheeks get even redder.

Jess’ eyes lit up when she saw Sam and she smiled a mile wide when she saw that Sam was with Dean. She didn’t seem to notice the abject horror Sam was experiencing until she had approached the table. She twisted her head a little and narrowed her eyes.

“Do you two know each other?”

Dean burst out laughing.

Jess stared at this bizarre behavior and Sam glared but Dean could not stop laughing, even though even he wasn’t quite sure why.

“Did I miss something?” Jess asked after a moment, and Sam sighed as he  nodded. Dean was finally calming down and took a swig of his beer before he nodded as well.

“Yeah, not that it’s any of your fault. I’m sure Sammy here doesn’t have any Polaroids up of the two of us or anything,” Dean said, with just a hint of feeling snide in the layer of humor in his voice.

“Oh my god, are you two exes?” was Jess’ next question. She didn’t let either of them get a word in before she continued. “I mean, Brady was one thing, but this guy’s like a model, Sam. Did you just like find an Abercrombie to pick guys up at before? If you did you have to tell me‒”

“Oh my god, Jess, please stop,” Sam finally said. Jess immediately snapped her mouth shut. She looked chastised and Sam would have felt badly if he wasn’t more concerned about the mild look Dean was giving him.

“Huh.”

“What, Dean? What?” Sam demanded. Dean put his hands up in a move of surrender. Neither of them was looking at Jess, who was watching the back and forth between them with a look of utter bewilderment.

“Nothing,” Dean defended. “I just said ‘huh.’ Is that a crime now?” Sam’s lips whitened as his expression turned even angrier. Dean rolled his eyes to the ceiling before sighing and furthered his answer. “Just didn’t realize you were playing for both teams is all.”

“I’m not exactly‒”

“Okay, enough,” Jess interrupted. “Before you get into talking about being a two and half on the Kinsey scale, will you please tell me what the hell is going on?” She paused to look between the two of them. “How do you two already know each other?”

Sam and Dean shared a look and Dean shook his head. “She’s your girlfriend. You tell her. I’m going to get more alcohol.”

Dean moved to get up and Sam rolled his eyes.

“Get me a beer,” Jess said as Dean walked toward the bar. He waved a hand behind him in acknowledgment. Jess turned to Sam. “Now spill. What the hell’s the deal here?”

Chewing his lip briefly, Sam looked almost defeated, but he seemed okay when he met Jess’ eyes. “Jess, that’s my brother.”

“Oh my god,” she responded. She looked shocked. “I didn’t even think about the name.” She shook her head, gaping a little. She turned her head and stared at Dean where he was waiting for another glass‒ he’d just gotten a pitcher of beer and out of the corner of his eye Sam had seen him take a shot‒whiskey probably. “That’s your big brother. Who hasn’t ever come to see you and has called what, twice since you’ve been at Stanford?”

“To be fair, he’s drunk dialed me a few times more than that,” Sam amended, and then tilted his head a little to nod, “but yeah, that’s my brother, Dean.”

“Oh my god,” Jess repeated. “Now I feel really bad about the comment about sitting on his face.” Sam laughed at her mortification. “Now I feel really bad about this whole thing actually. God, it’s one thing if a girl wants to bring another guy into the bedroom, it’s a totally different thing if he’s your older brother. Talk about an ego blow.”

“Jess, no, don’t worry about it,” Sam protested. He took her hand. “For one, the face sitting comment isn’t even the worst thing I’ve heard someone say about Dean. And for two, it’s not a blow to my ego at all. I mean, hey, we’ve got the same genes so maybe it’s an ego boost.” He was smiling at her and shrugged at the last part, pleased when her dismay turned to a light laugh.

“We might have the same genes, but you and I both know I’m the pretty one,” Dean said as he came back with the pitcher of beer and three glasses. Sam gave him an annoyed look and then Dean was the one to shrug. “I’m just telling it how it is, Sammy.”

“You’ve got to stop calling me Sammy. It’s Sam.”

“Yeah, whatever. You gonna actually introduce me to your girl or are we supposed to go on the introduction we already made? The one where she made it very clear that she wants to see me naked.”

“Could you not?” Jess said. Dean threw a cheeky smile her way and she refused to respond to it until he’d had enough and dropped it. Jess would try not to hold it against him that he rolled his eyes a little bit there. She also was trying not to acknowledge the part where she still definitely wanted to see him naked. Maybe even a little bit more in light of recent information.

Sam looked pissed, but he went through the motions anyway. “Dean, this is my girlfriend, Jess. Jess, my brother, Dean.”

“Well it’s nice to meet you, Jess,” Dean said in a tone that belied the truth of the situation. “Now that I know who this boyfriend of yours is, I’ve gotta tell you that you’re definitely out of his league.”

“What, and in yours?”

“Well, I am like a model,” Dean said with a grin, parroting her earlier words back at her. Jess’ face was flat and Sam didn’t look too pleased either and Dean shrugged after a second of their stares. He waved a hand and took a gulp of his beer. “I’m just joking around. For a couple who were looking for a third, you’re being a little uptight.” Sam and Jess shared a glance. “And not even a second girl. I mean, you were going pretty full out with the kink.” Dean paused and threw a half grin at Sam. “Hell, I’m almost proud.”

Sam tried to turn a laugh into a scoff. “Shut up.”

His half grin turned into a full one before he said, “Come on, sit down. We’ll drink and deal. You can tell me all about how great college is, what your classes are like.”

“You don’t care about what college classes are like at all, Dean,”

“Yeah not at all, but you can tell me about ‘em anyway if you want.”

“How many beers have you had?”

Dean screwed up his face in an expression that clearly asked Sam what difference that made, but he answered anyway. “This is my fourth. I’m not drunk, man, come on.”

“Are you sure? I mean, we can just go?”

Sam regretted it the minute he said it; he could see the hurt in his brother’s eyes. He also looked ready to snap back at him when Jess intervened.

“No, come on, Sam. You never get to see your brother, let’s sit. We’ll have some beer.”

“See, listen to your girl. She’s clearly got more sense than you,” Dean said with a point of his whole hand. He turned a smile on Jess and she definitely had a difficult time not thinking _yep, still want to sit on his face._


	2. Chapter 2

Jess and Dean got along way too well for Sam’s comfort, not because he didn’t want them to get along and not even because they decided to gang up on him in a game of darts because Jess was getting her ass kicked and Dean thought he’d be able to even the score out for her‒which he did, of course‒, but because somewhere in the back of his mind was the niggling sensation of worrying what it said about him that they seemed so compatible. He knew he’d left for reasons that had nothing to do with Dean, had maybe quite a bit to do with John, but had the most to do with the life, but it still felt strange for him to think about the idea that he’d found someone to stand in for Dean, even in a completely different way. Of course, it was probably just the alcohol talking; Dean had insisted on making sure Sam was drinking steadily, making some excuse about not having been there to get him his first legal beer.

“You got me my first beer was I was 14,” Sam had pointed out, but Dean hadn’t taken it as an excuse. Which meant that now, Sam was willing to admit that he was on the verge of drunk.

He’d forgotten what it had been like sometimes when John was away on a hunt and he and Dean were left to their own devices with each other. The summer Sam had been 16 and Dean 20, they’d been stuck in a rickety old cabin some Marine buddy of John’s had let him use for a month while John went after some monster. The hunt had suddenly turned into two hunts and nearly turned into a third if that buddy hadn’t come calling to use the place and forced John to come get his boys‒ two months later, John had given Dean the impala and gotten himself the truck. The cabin had been drafty at night and sweltering in the day, but it was less than a mile away from a lake and nothing else and sunshine seemed to have been abundant in Wisconsin in ‘99 so suddenly, Sam and Dean could remind each other what it was like for them to be friends. That summer flashed in and out of Sam’s thoughts throughout the night.  This was a better reunion with Dean than he could have ever imagined, but he suspected it had to do with Jess’ presence and with a severe lack of a hunt on Dean’s end. Sam didn’t really care why, either way.

“Comic books just weren’t my thing, growing up,” Dean was shrugging at Jess.

“You’re telling me you don’t have a preference for DC or Marvel?” Jess asked.

Sam puzzled and wondered how they had stumbled onto that topic this time; Jess may have given him crap about having been about to say something about being a 2.5 on the Kinsey scale, but she was notorious for working female comic book heroes into conversations with guys like Dean.

“Jess,” Sam said, a smirk on his lips, “He’s not going to know who Mockingbird is, you don’t have to defend her to anyone. He’ll take your word for it.”

It was clear both Jess and Dean would have responded to him, in different ways, but they were cut off by the announcement that it was last call, and they’d better make sure to pay their tab as well, from the bartender. Dean stood up from the stool he’d been in and dug his wallet out. Jess held up a hand to protest but Dean pulled out a credit card and waved it around, quick enough that she couldn’t see the name “James Page” on it, but Sam knew what it was. He opened his mouth to protest as well, but Dean _winked_ at him, the cheeky bastard, and sauntered off toward the bar. Sam shook his head a little, his tongue behind his upper molars. Jess put a hand on his arm.

“Sam,” she started.

“Jess,” he replied; she looked so earnest he couldn’t help it.

“I know that part of finding a second guy was for you too, if you decided you wanted to go that far, but‒”

But Jess cut herself off as Dean was making his way back to their table. Sam suspected he knew what she’d been about to say though, and he wasn’t sure how he felt about it.

Dean was smiling at Jess, his head tilted a little. “So, you two got a couch I can crash on?”

Jess looked at Sam, and Dean made it clear he didn’t want Sam to see him glance his way as well, and Sam spoke up. “Yeah, you can crash on the couch.”

“Okay, good, I’ll follow you then.” Dean was already fishing his keys out of his pocket, the jangle of them as familiar as a lullaby to Sam, even after years without having heard it and any sane person saying that keys all sounded alike.

Jess snorted a laugh. “Then you’re going to be following a bus. Neither of us has a car.” Dean made a face. “What? Something wrong with the bus?”

“Only that it’s not a car.”

Jess shrugged. “I never really got the obsession with having a car. It’s much cheaper to have a bus pass.”

“Less reliable,” Dean explained. “Plus, not everywhere has a bus, city girl.” Jess nodded to concede her point and she held her hand out. Dean looked down at her hand and furrowed his brow. Jess jiggled her hand a little and Dean’s furrowed brow turned into a shocked expression. He raised his eyes to Sam. “Does she think she’s driving my car?”

“She has had the least to drink. That was always dad’s rule too,” Sam said. Jess tried to hide any concern that that statement raised and Dean looked almost exaggeratedly offended.

“You never wanted to follow the man’s rules then, but now, when _some stranger wants to drive my car_ you want to follow them?”

“She’s not a stranger‒”

“A stranger who doesn’t even have a car of her own?”

“I do know how to drive, Dean. Just didn’t need to much,” Jess explained. “Give me the keys or you have to take the bus too.”

Dean blinked at Jess, aghast and unable to react any more strongly than that. Sam shook his head in disgust and plucked the keys from Dean’s hand; Dean reacted too late to try to close his fist.

“You got that slow?” Sam asked, handing the keys to Jess and Dean looked between the two of them.

“No,” Dean’s reply was clipped while he stared at the keys in Jess’ hand. “You know I’m not that drunk.”

“Oh my god,” Jess complained. “It’s less than two miles, I won’t ruin your precious car.”

Sam took back everything he’d thought about Jess and Dean seeming too similar. Dean looked positively stricken with grief as he trudged out of the bar behind Sam and Jess and Sam rolled his eyes at his brother’s antics.  

There were only two cars in the lot and Jess was smart enough to know that Dean’s wasn’t the one with rust spots all along the bottom of the doors and the UFO bumper sticker. Jess was sure to grin the entire time she was settling into the driver’s seat and it just made Dean’s pained look more pronounced. Sam hated being in the backseat again.

*

The corners of Dean’s mouth turned down in consideration when they got into the apartment. He looked around nodding a little bit.

“Not too shabby, Sammy.”

“Still just Sam.” Dean rolled his eyes.

“Where’s your can?”

“Classy. Last door on the right down the hall,” Sam told him with a point of his finger. With a nod of his head, Dean was off. Jess was shutting the door. “Did we put the extra pillows back in the linen closet after the last time Chanel had to stay here after one of your wine nights? Or are they still in ours?”

“Ours,” Jess answered with a dismissive wave of her hand. “But I don’t want us to need them.”

Sam cocked his head a little, his eyes narrowing a slight fraction as well. “So, you want Dean to leave then?”

Jess sighed and she wrung her hands a little. She stepped closer to Sam and he did have to tilt his face down a little to make sure he was looking her in the eye. “You know that’s not it. And I know this is too much and you can shoot me down right away if you want but‒”

“You still want him.”

“I want him for this,” Jess corrected. “You didn’t see it tonight because well, you couldn’t, but Sam, you and Dean maybe haven’t talked in a long time, but you were on the same wave length more than a few times.”

“So?”

“So can’t you imagine how hot the idea of that is for me? Part of this was for you, yeah, but in all fairness this one is my fantasy. The workshop was step one for your fantasy, which I’m also really excited about, but the threesome was my pick.” Sam hadn’t even opened his mouth to reply before Jess had more. “It’s not just my decision though and I don’t want it to be, but I wanted you to know so I had to bring it up.”

“Jess, I can’t have sex with my brother,” Sam said, his voice flat. Jess was shaking her head.

“I’m not asking you to. Not in the way you meant. I’m not asking you to do anything you’re not comfortable with, but Sam, the idea of you both at once, like, riding his face while I suck you off, is so hot to me.” Somewhere in her statement, Jess had started to run a finger up and down Sam’s forearm.

“Yeah?” Sam asked. One of his hands came to rest on Jess’ waist and his thumb rubbed circles into her stomach. Jess nodded.

“I still want this.”

It was at that moment that Dean chose to return, wiping his hands on his jeans and coming up short when he took in the scene.

“Do you two want the couch then? Because I’m more than willing to sleep on a bed.”

Jess didn’t turn and look until she saw an infinitesimal nod from Sam, but then she faced Dean and detached herself from Sam’s hand.

“There’s probably a delicate way to say this and ask this, but do you think you’d still be willing to be a part of a threesome?”

Dean turned his head out as though he wasn’t quite sure what he’d just heard. When Jess didn’t repeat herself he asked, “With you two?” Jess looked back at Sam again and then turned and nodded. “You and my brother, you mean?”

“Yes.”

Dean was looking at Sam then, trying to gauge his reaction and while there was some color in Sam’s cheeks, and his hands were shoved into his pockets, he was more than willing to meet Dean’s eyes and he looked calmer than he probably should. Dean chewed his bottom lip a bit, worrying it between his teeth until it almost hurt. Jess and Sam remained silent and waited. Finally Dean asked his brother, “You sure you’re okay with this?”

Sam started a bit at being addressed. His hands came out of his pockets. “If we have some ground rules, I think it could work out alright. I mean, if we’re being honest, it’s not like I haven’t seen you have sex before. You were terrible about locking the door for a while.”

Dean cracked a smile. “That one time you saw more of Roxanne than you did me.”

“Yeah, I didn’t forget.”  Sam was still smirking and Dean threw his hands up a little bit.

“Fuck it. I’ve probably done worse.” He shot Sam a warning that kept him from making suggestions as to what had been worse and then looked at Jess. “How do you wanna do this, boss?”

“I haven’t really decided,” Jess admitted. Dean nodded.

“Just as a suggestion, you could come over here. Let me kiss you and you decide if you really wanna do this at all.”

“Is it gonna be that bad of a kiss?” Jess joked before she stepped toward him. Dean smirked.

“Sweetheart, I meant whether or not you wanted to ditch Sammy all together.”

“Hey!” Sam protested as Jess laughed a little at the gall Dean had. Jess was right in front of Dean when she stopped laughing and it did feel a little bit like the air in the room had gotten thinner. She expected Dean to wrap an arm around her waist and yank her to him, pull her into a filthy kiss that she’d feel go through her, but he stood for a moment and just searched her face before he brought a hand to her cheek. The heel of his hand cupped her jaw and the pads of his fingers tangled in her hair and he didn’t move from there still. He was nervous, Jess could feel it.

“I thought you said this wasn’t your first rodeo,” she said lightly.

“It’s not, but I’ve never kissed my brother’s girl with his permission either.” He saw Jess’ eyes go wide. “I may have snaked his prom date. In my defense, she had sort of dumped him.”

“Dean,” Sam said warningly. Jess saw out of the corner of her eye that Dean reached behind her and lazily flipped him off.

“Well, I’m not dumping him. He’s part of this, but you might not be if you don’t quit being scared and kiss me,” Jess said. It was an obvious tactic, but it worked.

Dean leaned down and slotted his mouth over hers and it was soft and gentle and Jess was struck by how differently her first kiss with Sam had been until she was distracted by Dean’s tongue touching the seam of her lips to work its way inside her mouth. She opened her mouth under his and the kiss deepened and even though it wasn’t the filthy pornstar kiss she’d expected, she felt it melt through her. That melt turned into a downright burn when Dean’s other hand came up and wrapped around her, landing on the small of her back and sliding up under her shirt just enough to tease. His fingers pressed into the spot between her back dimples and she heard herself give a little hitch in her breath. He broke the kiss there.

Jess stared at him for a moment, searching his face for any sign of question. She was shocked to find that there wasn't any. He looked back at her calmly waiting her assessment. She took his hand and turned out to face Sam, holding out her other hand for him.

"Yes," Sam stepped forward as she spoke, and took her waiting hand. "I want to do this."

Sam nodded and he stepped past her, leading them to the stairs and up them, Jess with Dean in tow. Jess could feel the differences in their hands. It wasn't just that she was used to Sam's hands, huge and college boy smooth made that way by holding pens and typing papers and curling around solo cups at the frat parties she dragged him too, and Dean's were a foreign country she'd never been to but wanted to visit, it's that they were shaped differently, as though each of them was made to be doing what they were doing. Jess remembered the first time she'd held hands with Sam, his hands had the same callouses as Dean's did now, but on the verge of healing. She'd never thought they were meant to be that way. She had no idea how either of them had ever gotten those callouses, but she thought maybe she'd ask. But later. Right now she just wanted to feel those differences on her, even though they'd both be warm and sure.  Sam nudged the door of their bedroom open and tugged the pair of them in right after him, giving no one time to second guess. He pulled Jess right into his arms as well, kissing her thorough and hot when he did. Jess' one hand was still tangled with Dean's and he rubbed his thumb back and forth against her wrist as Sam's tongue opened her mouth up for him to explore. Jess felt his hands snake to her ass and she could hear Dean clear his throat a little pointedly.

Sam pulled away from the kiss, letting his hands still rest on Jess' backside and he almost sent a challenging look at his brother. Dean's response was to tug Jess toward him and into his own arms. She willingly followed and was surprised when he immediately walked them backwards until Jess back hit Sam's chest. She could feel every movement of his pecs against her back as he brought his hands back up and settled onto her waist. Dean smirked before he kissed her, less gently than before, and he rucked her shirt up to just below her breasts, sliding his calloused hands against her ribs and Jess gasped a little into his mouth. She ground her hips backwards into Sam and felt him starting to grow hard in his jeans as Dean moved from Jess' mouth to her jaw down to her throat and she bared it up for more, hoping to feel his plush lips everywhere. What she got was Sam leaning down to kiss the other side of her neck and her hips went back into his again.  

She put a hand on Dean’s shoulder and he straightened up off her neck. Sam straightened up as well when he felt Jess’ hands go to the hem of her shirt and start to lift. As soon as the fabric hit the floor, Sam’s mouth found her shoulder and kissed.    

Jess found herself straightening up as she felt Dean’s eyes roam her body, drinking her in. His tongue darted out to lick his lips again.

It made Jess bold and her lips curved into a small smile. Dean moved to stepped closer to her again, to kiss her no doubt, but she held him off with a hand up. He stopped immediately. Sam’s hand was still running up and down Jess’ side gently.

"Take my pants off for me, Dean," There wasn't a command in it, but she wanted there to be. Dean did step closer to her then and he ghosted a hand down her stomach until his fingers twisted open the button on her jeans and unzipped them without his eyes leaving hers.  “Sam,” Jess said, still not looking away from Dean while he deliberately inched the denim down her legs. “Please get undressed and sit on the bed against the headboard.”

Sam kissed her shoulder again. “Sure. But where are we going with this Jess? Ground rules.” Jess turned her head to look at him.

Dean paused in his removal of Jess’ pants and looked up. Jess whipped her head back around to tell him “that doesn’t mean you should stop” before she turned back to Sam and addressed him. “Okay, then lay them out.”

“One,” Sam started before he pulled off his shirt. “Dean and I don’t touch unless accidentally or unless necessary.”

“And it’d be great if you didn’t make it necessary, right?” Dean added. Sam agreed with a conceding nod.  

“Two, don’t talk about us being brothers while we’re doing this.”

“Isn’t that breaking the rules already?” Dean asked. He was lifting Jess’ right foot off the ground so he could have her step out of her pant leg.

“Shut up, Dean. Three, use our names if you’re giving a request. It’ll help with number one.” Sam closed his mouth and tossed his shirt into the corner; he’d been holding on to it still. Jess nodded.

“Okay, Sam. Is that it?”

“I think so.” Jess smiled and pecked him on the lips.

“Okay, good. Then, Sam, please get the rest of your clothes off and go sit on the bed at the headboard.” He grinned then and kissed her again. She turned to face Dean, who had finished taking Jess’ pants off, and had straightened back up.

“How come he gets a please?”

Jess gave him a calculating look. “Do you need a please?”

Dean couldn’t meet her eyes and if there had been decent lighting in the bedroom- not just the dim lamp that sat at their bedside table‒ Jess thought he might have been blushing. Her excitement spiked.

Sam was climbing onto the bed and he arranged himself with his back against the headboard and his thighs spread shoulder width apart. His hands rested over his lap, covering himself.

“You Winchesters must have a modest streak in you,” Jess mused. “You’re going to have to get over that. Dean, get naked.”

Dean didn’t hesitate and Jess wanted to moan at the way he looked when he ripped his shirt from his back and immediately set to work on getting his pants off.  Sam was all abs, but Dean was a little bit softer in the middle, just enough that they would feel different when Jess let herself be pressed against them, but she was still excited to feel Dean’s body against her own. Dean stepped out of the pile his jeans created on the floor, ungraceful and unabashed and Jess’ eyes roamed his body. Dean let Jess look, but he brought a hand to his cock and stroked slowly. Jess raised an eyebrow.

“Hey, if I’m gonna be on display, figured I’d give you the best show.”

“Oh my god, shut up, Dean,” Sam tried not to laugh. Whatever uncomfortable tension there’d been in the room broke at the sound. Dean smirked and Jess laughed.

“Let me help you with that,” she said and stepped toward Dean. “Dean, stop. Hands off.”

Dean dropped his hand as Jess reached him and brought her hand up. She didn’t touch him, just waited to see how Dean would react. His leg twitched a little and Jess smiled then. She wrapped her hand around him and watched his face as she twisted her wrist when she got to the head. His pupils were widening and when she made the same motion he hummed a little sound of pleasure.

“Touch me.” Dean’s hands come up to Jess’ waist and teased at the edge of her panties, his fingertips dipping just below the top to brush the back of her hips. He skated one hand around and twisted his wrist so he could reach down the front of her panties and tease at her sex. One finger parted her lips and slid against her, cunt to clit. He only teased, taking his hand back out of her underwear and rubbing against her through them once he did. Jess was still slowly jacking him and Dean’s hips chased after her hand whenever her thumb brushed against his slit. “Stop.”

Dean stilled his hips and his hand fell away from Jess. His eyes dropped to her bra and went back up to her face with a question. She nodded and he had the garment off of her in no time. He made an abortive move to touch her newly bared breasts but stopped himself.

Jess jerked her head to the side to let Dean know to follow her as she made her way to crawl onto the bed, slipping her panties off in the process. Dean hadn’t followed her- she’d climbed right onto Sam’s lap and his hands had come to her hips and they kissed. Jess looked good naked and on top of Sam, her nipples grazing against his chest. She looked better when she turned out of the kiss and told Dean to get up and join them. “Go ahead and sit right next to Sam for now.”

Dean got onto the bed and sat next to Sam without ever looking at him, which Jess would have been impressed with if she hadn’t been busy kissing down Sam’s neck and bringing a hand to his cock. She could feel Dean’s gaze on her as she stroked Sam and their mouths slid together and when she backed out of the kiss to look at Dean, he was waiting. Jess nudged Sam’s legs apart so she could settle one knee between them and she did the same thing to Dean. Their legs were flush together but neither of them said anything about their ‘no touching’ rule as Jess’ hands were wrapped around both of them and she alternated between kissing each of them. The weight of each of their cocks in her hands and the way both of their hips twitched up to chase the friction was heady enough, but combined with the differences in how they kissed her, Jess felt powerful. She did until Sam surged forward and put his hands on either side of her face to kiss her intensely, controlling her mouth in a way that sent tingles down her spine. She rocked her hips against their legs and felt Dean’s hands come to her waist and egg her motion on. He kissed down her neck while Sam was still ravaging her mouth and Jess moaned. Her hands lost their rhythm completely when suddenly, without notice, they switched positions and Dean was coaxing his way into Jess’ mouth and Sam was biting at her neck, doing his best to suck hickeys into her tan skin.

Sam’s hands had coasted from Jess’ face down to her breasts, thumbs brushing against her nipples back and forth. Dean’s hands were squeezing the globes of her ass and pulling her hips into a quickened pace. She rocked herself back and forth and groaned into Dean’s mouth as Sam pinched at her nipples. Every part of her that they touched felt electrified and she wanted more. She’d barely had the thought when Sam’s mouth dropped from her shoulder to her breasts and he suckled on a nipple as one of his hands fell to circle her clit, rubbing her slickness against the nub opposite her rhythm so she was constantly stimulated. Sam kept the pressure just the way he knew she liked and Dean cocked his leg up just a slight bit as he kneaded into her ass and Jess knew she was whining at how close to coming she felt. Dean moved his mouth from hers to her earlobe, nibbling, and with Sam’s continued ministrations, Jess felt herself go over the edge into orgasm. Her grip tightened around Sam and Dean and she heard Sam hiss.

“Shit, sorry,” she huffed out before she kissed Sam in apology. Her hips were still bucking in aftershocks and her hands had stopped moving, just wrapped around Sam and Dean’s cocks, the weight of them solid and warm as she rode out her orgasm, her muscle contractions calming down.

“’S’alright,” Sam slurred against her ear. “Will you suck me?”

Jess nodded absently. “Dean, lay down on your back. Head in the middle of the bed.”

Dean didn’t ask why, just complied, one hand going to his dick and popping the head in and out of the ring of his fingers with a jerk of his hips once he was on his back. His head was tilted up to look at Jess as she kissed down Sam’s torso, her tongue flicking at his nipples.

“I want to sit on your face, Dean,” she said when her mouth wasn’t attached to Sam’s skin.

“Oh, hell yes,” Dean said, one hand reaching up and grabbing at one of Jess’ thighs. She slapped it away, none too gently.

“I’m the boss, remember?”   

His brow furrowed and he pouted a little, but he didn’t make a move to grab her again. Jess continued to kiss down Sam’s torso and traced the line of his abs with her tongue, the muscles there jumping a little in response. The crown of Sam’s dick bumped against her neck and she smiled against his skin.

“Don’t be a tease, Jess,” Sam told her. She smirked up at him and he just raised an eyebrow expectantly. Jess smiled outright, as always, loving that Sam, who was infinitely patient with her and sweet, wouldn’t brook her teasing in the bedroom.

She licked a stripe up from the base of his cock to the slit before popping the head into her mouth. Sam tilted his head back and bit his lip at the concentration of suction around his head. She kept it up and flicked her tongue out against his slit and he brought a hand up to tangle in her hair, just resting there. Jess hummed a little in appreciation and Sam was just about to put a tiny bit of pressure on her head to let her know that she could move at any time, when he felt a flick against his upper calf. His head snapped down and he glared and Dean, who wasn’t even trying to pretend he hadn’t done it on purpose.

“You’re kidding, right?” Sam asked with a groan. Jess pulled her mouth off Sam with a faint pop and Sam groaned again.

“Well, I didn’t mean for her to stop really,” Dean said in his defense.

“Oh, Dean, you interrupted the flow,” Jess said in disappointment. “You know you ought to be punished for that.”

The eagerness that flashed in Dean’s eyes was obvious though he tried to hide it.

“I was just gonna let Sammy know I was gonna move. I mean, you’re the one who wanted me to eat you out and I’m laying here without tasting a thing even though I can smell how good it’ll be.”

“I wish you wouldn’t talk,” Sam sighed. Jess smiled at him and turned a glare at Dean.

“Dean, move. Lay between Sam’s legs, exact level you are. Sam, spread your legs a little more, please, baby.”

There was no way for Dean to look graceful as he maneuvered himself into position again and looked pleased with himself, but he didn’t seem to mind. One hand went back to lazily stroking his dick as he tilted his head to look up.

“Jesus, Sam, your cock looks huge from this angle.”

“Oh, my god, shut up,” Sam whined. Jess leaned forward and kissed Sam briefly and he murmured against her mouth, “Please shut him up.”

“Sam thinks I should shut you up,” Jess told Dean over her shoulder. “I agree with him, but this isn’t a reward for acting without permission, Dean. I told you I was the boss and Sam told you not to touch him so really, I think you shouldn’t get to touch your dick while I ride that mouth of yours. So hands off, sweetheart, and you might want to take a breath.”

Jess heard Dean whine, but he did unwrap his hand from his cock and lay it against his stomach. She moved herself down the bed until she could feel Dean’s breath against her and she waited a second to see if Dean would reach his neck up to lick at her, but he didn’t.

“Good boy. You wait until I come down there on my own,” Jess told him before she bent and took Sam’s cock back into her mouth. She sucked him down to the base immediately and his hand wrapped back in her hair and held her there. She gagged a little and pulled back to breathe only to dive back down and do it again. Over the sounds of her gagging she could hear Sam moaning “oh, fuck, Jess, fuck.” She gasped when she came back up for air and stroked Sam’s now filthy wet cock.

“Oh god, Jess, I want you to suck me,” Sam groaned. Jess looked up at him as she sucked him back into her mouth and stroked her hand up to meet where her lips were wrapped around him. Sam met her eyes and rubbed his hands across her shoulders, chewing his bottom lip while his stomach muscles jumped. They could all hear Dean groaning over the slick sounds of Jess sucking Sam’s cock and Sam’s breathing.

Finally Jess took pity on Dean, or she grew too desperate to know what his mouth felt like on her and she lowered herself so Dean could taste her sex. She moaned around Sam at the first touch of Dean’s tongue to her entrance, but moaned even longer when he ran his tongue up to her clit. Her hips moved on their own as she bobbed up and down to suck on Sam, rubbing her sex against Dean’s lips and tongue.

The moans Dean was making sent vibrations through Jess, especially strong ones when he puckered his lips around her clit and suckled. Jess cried out, slipping off Sam’s cock for a moment, losing her rhythm in how good the pressure on her clit felt. She breathed, ragged, and pulled Sam back into her mouth, tonguing at the bundle of nerves at his cock head the same way Dean was tonguing at her clit. She felt Dean’s arms suddenly wrap around her thighs and still her hip’s movements. She couldn’t protest with the sudden onslaught of sensation, Dean somehow finding a way to stimulate every part of her, nose against her clit and tongue fucking in and out of her cunt, lips against her opening.

Dean’s elbows dug into Sam’s thighs and they were warm against him, but Jess’ mouth was hot and wet against his dick and she sucked him in tighter, her cheeks hollowing. His hand was in her hair again, the other reaching around to tease at her nipples, and he couldn’t stop himself from pressing her down until her mouth met her hand where it was wrapped around the base of him. His hips snapped up on his own accord and he felt his head bump against the back of Jess’ throat and he wanted to apologize, like he always wanted to, but his hips snapped up again and Jess was groaning and gagging a little and Sam wanted to scream out it was so good. Jess huffed a breath through her nose and her throat tried to swallow on its own accord and he groaned out a warning enough for Jess to take another breath and then swallow down his spunk as Sam came.

Dean was still licking at her, pulling her down against him when Sam hauled her face up and kissed her hard, hands both finding her nipples then and rolling them. He kept kissing her and kept playing with her nipples and Dean kept eating her out with his hands around her thighs, fingertips digging into her hips and she was coming again, crying into Sam’s mouth at the strength of her orgasm. She felt rather than heard Dean’s high keen as she came and he kept licking her. She tried to pull away from Dean and he tried to keep her there, keep his mouth against her but she whined again and he dropped his arms. Jess tipped over to the side breathing heavily when Sam let her go. He was breathing heavy too, sitting back on his heels and staring at Jess.

“Oh, fuck, please touch me,” Dean cracked after a moment where it looked like Jess was zoning out. “Please, Jess.”

“Oh, fuck, Dean, of course, baby,” Jess said hurriedly, unthinkingly. She laid herself next to him and kissed her own taste from his mouth and stroked his cock, grip sure and tight and her thumb brushing against the head with every twist of her wrist. She kissed against his jaw. “Will you come for me? You made me feel so good, will you come for me?” She asked between kisses, filthy and open mouthed and hot against his skin. “You did so good, you’ve got such a good mouth and made me come so hard, Dean, I want you to feel good too. Come for me.”

The question left her voice and she twisted her hand so she could brush against Dean’s balls before she stroked him again and let precome slick her way. “Come for me, Dean,” she said again and Dean’s hips rose off the bed as he came, wordlessly with his mouth open.

“You did so good,” she murmured and pressed a kiss against his temple and then against his mouth. She sat up and kissed Sam gently before standing.

Sam and Dean didn’t say a word to each other while Jess was out of the room. She came back with a damp washcloth and shook her head when Dean held a hand out for it.

“I’ll clean you up. You were so good for me, it’s the least I can do.” She was gentle as she wiped the come off his stomach. She folded the rag over and wiped across his forehead as well. He made a face and she smiled. “Also, sorry about calling you baby. Habit.” She looked up at Sam. “I suppose I should be saying sorry to you though.”

Sam shrugged and Jess got up again. She tossed the washcloth into the hamper in the corner and jerked her head at Sam. He scooted to one side of the bed.

“Dean, can you get up  here so we can sleep please?”

“Now I get a please?” Dean grumbled as he shimmied up the bed and to the opposite side where Sam was. Jess just looked at him pointedly and crawled in between the two of them. She pulled the blankets up and turned onto her side, spooning Sam. Dean would have laughed about his brother being the little spoon, but he and Sam had had to share a bed for so long that he wasn’t really surprised if Sam was used to it.  There was a tension in the room, one that Jess’ yawn didn’t break.      

“Well, that was fun,” Jess said sleepily. Her arm was around Sam’s waist and her legs were tangled in his but she turned her head to look at Dean. “You’re more than welcome to come back and we can do it again. Try something different next time.”

“Oh, yeah?” Jess nodded at his question and he went on. “How’s Sam feel about that?”

“If she wants you to come back and you want to come back, you can, Dean,” Sam answered quietly after a moment. He could feel Jess curl her mouth into a small smile. He flicked his eyes to the side and caught his brother’s gaze. Sam’s eyebrows twitched in the equivalent of a shrug and Dean gave the same expression back.

“Now that we’ve got that settled, can we go to sleep?” Jess said. She yawned in the middle of whatever she said next, but Sam thought it might have been an offer of omelets in the morning. She didn’t bother repeating herself and she was out in no time.

“Was that weird?” Sam whispered.

“Only a little,” Dean answered back at the same volume. “We’re alright.”

“Okay.”

“Okay.” Dean adjusted his position a little. “Get some sleep, Sammy.”

It took Sam a little longer to get there, but he slept just as deeply as Jess did. When they both woke up in the morning, Dean was already gone. It wasn’t a surprise.

The note on their kitchen counter that said “Thanks for the freak fest. See ya around” was.


	3. Chapter 3

[Art](http://archiveofourown.org/works/3449006)

 

It was only three months before Dean came back again. Sam answered the door thinking it’s the Chinese food they ordered, gaping when it was his brother, a bruise high on his cheek and blood on his jeans.

“Are you okay?” was the first thing out of Sam’s mouth. Dean screwed up his face in confusion.

“Yeah, I’m fine. Why?”

“Well for one there’s blood on your pants. For two, you’re here.” Dean looked down at his jeans, noticing the blood.

“I thought I had an open invitation to be here. And you got a washer in this place? Haven’t gotten to stop for laundry in a while.” Sam was just about to scoff at his brother when Jess called out.

“Is our food here already?” She came around the corner and grinned in surprise when she saw Dean. “You’re not our usual delivery guy.”

Dean’s smirk was a mile wide. “I’m holding back a lot of great porn jokes right now, you know that right?”

“This is reality, Dean,” Sam reminded him.

“Buzz kill,” Dean muttered at his brother as Jess approached him for a hug. She wrapped her arms around him and when she pulled back made a face.

“You smell like a nasty bonfire.”

Dean shrugged. “Been on the road for a while.”

“Oh, yeah? Where?” Jess asked. Dean shrugged again.

“Here and there. Texas, Arizona.” Before Jess could ask anything else, Dean’s eyebrows popped up in a question. “Mind if I use your shower? I wouldn’t want to make a mess of your place while you ate.” He tacked a smile onto the end of it, all charm.

“Yeah, go for it,” she said and pointed a finger down the hallway. Dean nodded in thanks and started stripping off his over shirt as he walked down the hall. His belt buckle clanked as he undid it. As soon as the door slammed, Jess wheeled on Sam. “Is he alright?”

“He said he is, so yes?” Sam shrugged.

“Sam, there was blood on him.”

“Just his jeans.”

Jess looked unimpressed with that information, but Sam wasn’t going to share his worries with her; besides, Dean was there, so he hadn’t been too badly hurt. Sam just shrugged at Jess again and she sighed. She started to breeze past him, muttering about getting herself a beer, when she turned with a gleam in her eye.

“I kind of want him to fuck me this time.”

*

By the time Dean came out of their bathroom, hair spiked up with water and a wet spot forming where his t-shirt was stuck to him, Sam and Jess were picking their way through the cartons of Chinese food.  Jess had a swig of beer left in her bottle and she nearly spilled it down her chin when she went to set the bottle down too quickly as Dean came into view.

“Why’d you even bother getting dressed?” she asked as she wiped her mouth with the back of her hand. Dean looked down at himself confused.

“It’s a black t-shirt, you can’t see nipple or anything.”

Jess rolled her eyes. “Don’t be dumb, I meant get naked.”

Dean looked taken aback, blinking at Jess before turning to look at Sam, who had a forkful of food halfway to his mouth. He shoved the food in and was chewing when he responded.

“Don’t look at me.” Dean turned back to Jess and his stomach took the opportunity to growl loudly. Sam turned to Jess too, his sympathy for his brother clear on his face. “Let him eat first.”

Jess nodded and then jerked her head toward the third chair at the table for Dean to sit down. He did and swiped a pair of chopsticks that were on the table. He speared the food on the end of them instead of using them normally, a piece of chicken and a hunk of pepper the only things he could get with one stab.

“So that’s how it is? You boss me around, Sam bosses you around?”

Jess and Sam met each other’s eyes, Sam surprised and Jess contemplative.

“Sam doesn’t really let me boss him around in bed,” Jess answered. “I don’t really need to a lot. Plus, I think he’s hiding the fact that he gets off on being dominant‒”

“Hey!”

“You need to just admit it, Sam. I don’t mind it at all. But I also don’t mind giving the orders.” Jess shrugged as she explained. She smirked before she went on. “Besides, you just scream ‘sub.’ Lotta posturing,” she laughed.  Sam snorted at that and Dean wrinkled his brow in offense. Jess huffed at Dean’s look. “Don’t deny you like being told what to do in bed. I watched you come at my command.”

Dean shoveled food into his mouth, lifting the carton and using the chopsticks to just push a mouthful in. He chewed and didn’t acknowledge Jess’ statement. He wouldn’t look her in the eye and it was obvious.

“You know,” Jess started. “If you wanted, we could make that arrangement a little more formal. You could just sub for me, without us having to negotiate it every time. If you wanted. It wouldn’t be too different from last time. Just a little less control. Little more defined, boundaries-wise.”

Dean made a show of considering it. “Yeah, alright.”

Sam let out a scoff. “Wow, eager much?” Jess swatted him on the arm for it.

“Hey, taking orders from a hot girl about how she wants you to fuck her is normal. It’s hot,” was Dean’s defense. His voice stayed steady, but his cheeks did redden just a touch.

“Like I said, Sam never lets me order him around.”

“Whatever, his loss,” He pushed the carton of food away and stood up from his chair to take his shirt off. He undid his pants so they were split open on his hips and spread his hands in front of him, offering himself to Jess. “I’m all yours mistress”

Jess scrunched up her face but stood up as well. “Okay, don’t ever call me that again.”

“Yes, ma’am.”

Jess whipped her shirt off and smiled. “Oh, that one I like.”

Dean made a good sub, obeying as best as he could while Jess rode his dick on the kitchen floor and ordered him to fuck her harder until she came and slid off him to fuck Sam too; he even waited his turn to come when she told him that.

*

It was Halloween when Dean showed back up. Sam was relieved to see him, hoping that his presence would distract him from the nightmares he couldn’t stop replaying in his head. It didn’t seem promising however when Dean responded to Jess’ excitement with a guilty look.

“You being here just gives me a reason to put my sexy nurse costume back on,” Jess said with a grinning leer.  

“I, ah, actually ‘m here on family stuff, Jess,” Dean told her with a hand rubbing the back of his neck. “Not that that doesn’t sound awesome, but, I gotta talk to Sammy.”

“Dean, whatever you have to say, you can say in front of both of us,” Sam protested. Dean shot him a look and cocked his head in a sort of shrug and then went on.

“Haven’t heard from Dad in a while.”

“So? He’s on a bender, he’ll be back.”

“No, Sammy, you’re not hearing me. Dad’s on a hunting trip, and I haven’t heard from him in a while.”

Jess felt the air in the room change and looked between the two of them. Sam swallowed audibly before turning to Jess.

“Jess, could you give us a second?” Jess looked completely put out by Sam’s request and he wanted to rectify it immediately. “Five minutes and we’ll come to bed, I promise.”

“Sam, why can’t‒” Jess started to ask before Sam went even further.

“We’ll be yours for the night. I’ll even let you boss me around.”

“Sam‒” Dean warned. Sam sent Dean a pleading look and Dean sighed and gave in with a nod.

“Dean can’t sneak out before breakfast this time,” Jess stipulated. She and Sam looked at Dean expectantly. Dean threw up his hands in exasperation.

“I’ll make you French toast as long you have the damn ingredients and Sam and I can take care of our business.”

Jess smirked at Dean and rolled her eyes before she crossed the room and planted a kiss on his cheek. There was a definite swing in her walk when she turned to head back up the stairs. Dean appreciated the view almost absently, on instinct. Jess turned once she hit the second step.

“Come to bed when you two are done. And don’t pretend you don’t want to.”

Sam and Dean both nodded at her before she turned and walked out of sight up to the bedroom. Sam turned his full attention on Dean.

“How long’s Dad been gone?”

“A few weeks, which isn’t that weird, but I can’t get a hold of him and he hasn’t checked in.”

“Well, where was he heading?” Dean shrugged. “What do you mean you don’t know? When’d you split up?”

“A while ago, Sam. You think I would be making pit stops here to fuck around with you and your girlfriend if I was with Dad? Come on.”

Sam straightened up completely. Dean stared at him in confusion as Sam’s face softened into sympathy. Dean held his hands out.

“I had no idea you’d been on your own for six months, Dean.”

Dean rolled his eyes. “Don’t throw the pity party just yet, I’ve been fine.” Sam looked unconvinced. “I’m fine. Will you come listen to the last message I got from Dad? Then of course we’ll have to wait to go after him because you go around making promises.”

Sam shook off the accusatory finger-pointing that Dean gave him and followed the way as Dean lead them out to the impala. He popped the trunk and Sam was hit with a wave of familiarity. Dean had been riding around in this car with all these weapons and no company for half a year and Sam had been living in his comfortable apartment with his girlfriend and worried about essays; he suddenly felt incredibly guilty. Dean went to hit play on the message and Sam stopped him.

“You know you could stay here,” he suggested quietly.

“What?”

“You don’t have to stay on the road and hunt on your own, Dean. You could make a life here. Or anywhere. But here you’d have us around.”

Dean looked at his brother hard. He heaved a deep breath. “Sam, I can’t play house with you and Jess when I’ve got a job to do.” Dean’s tone wasn’t quite as harsh as Sam expected. It was clear that he didn’t want to discuss it either way though.  “Now, listen.”

Sam did, brow furrowing at the sound of John’s voice, garbled in the message. “There’s EVP on there.”

“Way to go, college boy. I ran it through some more tests and this is what I got.” Dean played the message again and they both heard a woman’s whisper.

“’I can never go home,’” Sam repeated. “What the hell’s that about?”

“Beats me. But listen, come after Dad with me.” Sam didn’t even bother to ask the ‘what?’ that was obvious from his expression. “You’ll think of shit I can’t, and it’s Dad.”

“Yeah, and he told me‒”

Dean waved a hand. “Never mind what he told you. And don’t make a decision now. Doesn’t matter. You told your girl she could boss you around, and honestly, she seems like she’ll be pissed if she doesn’t get to.”

*  

“Jesus, it took you forever,” Jess complained when the door opened and Sam and Dean entered. “I almost got out my vibrator and said forget about you two.”

“Well, feel free to get it out anyway,” Dean told her. “Forget about us for a while.”

Jess shook her head. “And give you a free show without any work? I don’t think so. Especially not when Sam said I could be the boss.”

Sam looked a little nervous and opened his mouth to say something. Jess was rising from where she’d been lounging on her elbows on the bed and tugged Sam with her back to the edge of the mattress. She sat and kept Sam’s hand in hers.

“Don’t be scared, you know I won’t hurt you and you lay down the rules before hand. You can always refuse to do something I ask. That’s how being a sub in a relationship works, Sam. I love you,” Jess said and reached up to kiss Sam gently.

“I love you, too.”

Dean cleared his throat. Jess’ gaze went to him.

“You know that’s true for you too. You can refuse anything.” Dean nodded once. “Just safe-word out‒”

“Safe-word? We’re doing things that require a safe-word now?” Sam interrupted. His eyes were wide; Dean’s were too, but more out of excitement than concern it seemed. Jess filed that information away for later.

“Well, we don’t have to right now, but, I mean, Sam, we have talked about this before with just us. Maybe not tonight, but later, I could let you do some of the things we discussed to me, and I’d still be in charge of Dean so maybe that’d be a nice transition into it? Make sense?”

Sam was nodding in consideration and Dean held a hand up.

“Hold on, do I get a say in this at all?”

“If you were the one we were thinking of having tied up, sure.”  Dean shifted on his feet and jess felt a smile slide onto her face. “Which, judging by that not so subtle shuffle there, you wouldn’t mind being. So I’ve got kind of a weird idea.”

“Because this whole arrangement, our whole lives, aren’t weird enough,” Dean muttered. “Sure, what’s this idea?”

“I want to teach Sam how to be a dom.”

“What?” Sam asked.

“It wouldn’t be for every time, and if you don’t like it, we’ll stop.”

“What’s that got to do with me?”

“Well, Dean,” Jess said as she stood up, letting go of Sam’s hand to cross the room to stand in front of Dean. She trailed a finger down from his chin to his sternum. “I’ll be your dom so Sam can see how it’s done.”

“You mean more than ordering me to fuck you on a kitchen floor and not come until you say so?”

Jess grinned wickedly, and patted Dean’s cheek. “Oh, sweetie, yes.”

And that was how Dean found himself naked and achingly hard with his wrists bound together with a flimsy pair of handcuffs he could have easily slipped if he decided he wanted. Jess pinned his arms above his head since they had no place to attach them to their headboard, but the heat of her hands on him made Dean grateful for that. He would have slipped the cuffs without it. Jess had changed back into her Halloween costume and her breasts nearly spilled out of her top while the skirt tickled Dean's abdomen and thighs. She had foregone any panties and Dean whined with every brush of her slickness against his dick. She hadn't even begun to act like she was ready to fuck him, just kept teasing him with little thrusts of her hips up and down so she could coat his shaft with her wetness without ever letting him inside.

Sam was on the chair in the corner trying to pretend that he wasn't just as turned on by what was happening as Dean was. He couldn't see anything explicit- Jess was fully clothed, albeit revealingly, and she covered Dean's cock- but he could see the way jess would bite her lip every so often as she slid so that Dean brushed her clit and he could see the strain in Dean's neck as he tried not to whine and thrust up to get more friction. Jess didn't let up at all.

"See, now I know he wants to fuck me, and I know he doesn't wanna break down and ask for it, and you know how I know that?" Jess said for Sam's benefit. It of course had the added plus of teasing Dean and giving her even more power, so she was pleased as well. "Because he keeps giving these little hitches in his hips. They match how he's breathing. He's so turned on by not getting what he really wants right now."

Jess rocked her hips and groaned a little bit. She let her hands trail from Dean's cuff enclosed wrists down to his pecs, her weight leaning into him and making Dean groan too. She gave a light slap to one side of his chest and he groaned even more.

"Are you that kind of sub, Dean? A little pain going to help you get there?" Jess asked both teasingly and curious. "Because I can do that for you, if you want."

She scratched a nail down the center of his chest, lightly, and then followed it with her other hand, digging a red line into the skin that time. Dean hissed and his hips bucked a little, the angle hitting Jess just right.

"Oh, you are. But, I won't do that for you unless you tell me you want me to, Dean. I won't do it unless you ask awfully pretty. Otherwise, I can just grind myself off on you and see where that gets us. I'll be happy, but how will you feel? Still hard and desperate to come?"

"Jesus," Sam breathed out in the corner. Jess hadn't ever been silent in bed, but this was downright surprising, listening to her talk to Dean like this.

"Do you want to come, Dean?"

Dean nodded a little.

"Right now?"

Dean hesitated to move. Honestly, he just wanted to get his dick in something- Jess' cunt, her mouth, Christ, even his own hand, as long as he could quit being teased by not enough friction and glimpses of warm wetness. Jess smiled down at him and then turned to Sam.

"See, now he didn't say yes right away and that's the sort of thing you need to look out for. It's your responsibility as a dom to know what your sub wants and needs and to be good to them. Not so good that they forget who's in charge, but good enough that they remember this isn't all about power."

"Mmhmm," Sam nodded. Jess' hips had rocked faster as she spoke and Dean had groaned.

"Please, enough of the lecture and let me fuck you," Dean finally whined when Jess' hips were moving at a steady pace. She stopped moving altogether.

“That didn’t seem very polite,” Sam’s voice surprised them all, himself included. Jess turned and grinned at him. Dean looked almost betrayed.

“You stay outta this, Sam,”

“Now, that definitely wasn’t polite, Dean. You apologize.”

Dean looked absolutely scandalized.

"Come on, Dean. If you apologize it'll be good for you. I'll be good for you. Just because I'm in charge doesn't mean I won't reward you."

Dean pursed his lips and glared at Jess but she could see in his eyes it was mostly for show; just because she hadn't known Dean that long it didn't mean she couldn't read him.

"Sorry."

"Who are you saying sorry to?"

Dean cleared his throat. "Sorry, Sam."

Jess smiled. "See, now that wasn't so hard was it?" She turned to Sam before she continued on. "Now I know that you both act like you want to stay as separate as possible during our little escapades, but honestly, I think you ought to give up that game and admit that it sort of thrills you to have your brother around."

"Jess," Sam said, a light warning in his voice.

"But okay, I won't get into that today." She didn't bother to watch Sam mouth 'thank you.'

She started to move her hips again, rocking on Dean and he whined. He bit his lip

"See, now he's learning," Jess told Sam. "He wanted to protest, tell me that I said I'd make it good for him if he apologized but he held back. That deserves a reward."

She stopped rocking and leaned down to kiss Dean's neck, tonguing at his collarbone when she reached it. She continued to move down, kissing across his chest and sucking a pert nipple into her mouth.

"Uh, Jess?" Dean said after a moment. She popped up to look at him.

"This not doing it for you?" she asked, the change in her voice evident. She turned to Sam before Dean could respond. "Sometimes, you might break scene even if someone hasn't used the safe-word. Especially in new situations, or in situations where you're not super close, emotionally."

She moved a hand up to Dean's wrist where they were bound. He shook his head minutely and Jess didn't move towards releasing him again.

"Right," Dean nodded, placating. He didn't say anything for a moment. The three of them were in an odd tableaux; all three of them obviously turned on and in varying states of undress, Dean's cock lifting the front of Jess' skirt a little bit. In the silence, Sam was very aware of the strangeness. It was easier to deal with when they were in the midst of the sex. Finally Jess spoke up.

"What's up, Dean?"

Dean bit his lip and wouldn't look Jess in the eye for a moment. He cleared his throat before he answered. "I'd rather we didn't talk about rewards. Sort of makes me feel like a dog and I'm not really into that part."

Jess nodded. "Of course, we won't do it then."

"Thanks,"

"I can still blow you like I was going to though?"

"Oh, fuck yes."

Jess smiled cheekily. "Okay then, good. Now, are you ready to get back to being my sub?"   

"Yes, ma'am."

Jess kissed a line down the center of Dean's stomach, tongue dipping into his navel and she brushed her lips against his cock, light and teasingly before dropping her head lower to lick a stripe up his balls. She sucked one into her mouth and her hands stayed on Dean's hips and he cried out. He could feel her smile and he wanted to beg her to touch his cock. He didn't, holding strong though.

Sam had one hand wrapped around his own cock, stroking slowly. It should have felt as strange as it did when no one had been moving and they'd been discussing this as though it were an assignment, but he was too turned on by the way Jess looked, still in her nurse's uniform with her ass in the air and naked under the white of the skirt. He could see the slick she'd painted onto her own thighs and if he hadn't been told to stay seated where he was, he might have gotten up and gone to lick it from her. He was tempted to either way. He could see her lips stretched over Dean, his cock jutting above her forehead. Jess' eyes smoldered while she looked at Dean's head thrown back and his lips pressed together to keep from making noise. Sam's brain supplied him with the thought of what it would look like if he could see Jess closer at work, the way her cheeks would puff out if she took both of Dean's balls in her mouth, the way that'd look if Sam put his mouth on Dean's cock and looked into Jess' eyes and Sam had no idea where the idea had come from and it almost started him enough to take him out of being turned on, but the friction of his hand against his hardness didn't let that happen.

"Jess, please," Dean finally pleaded. He'd begged easier before, but now it seemed like a source of wounded pride.

"Please what?" she asked, popping her mouth off of him and licking around his other ball.

"Please suck my cock. Please."

"You Winchester boys sure do want my mouth on your dicks," she fake complained. "Do you want it enough to let me suck you both at once?"

"Oh, Christ."  

Jess laughed a little at his moan, but took no more time to swallow Dean's cock down. Dean let out a strangled cry that masked the one Sam let loose too. Sam stroked faster, matching the pace of the bobs of Jess' head. Dean's hips were thrusting up to meet her and Jess slammed her hands down onto them to still him. She pulled off of him after a gag, spit clinging from her bottom lip to his cock.

“I want both of you at once," she said, breathlessly. She didn't let either Sam or Dean fully react before she went on. "I want to keep sucking your cock, Dean, while your baby brother fucks me from behind, fucking me onto you more. Does that sound good?"

The teasing in her voice drove Sam mad. She had to know what she sounded like and he was up with his pants completely off in milliseconds.

"Is that what you want, Dean? Or do you want me to try to fit both you and Sam into my mouth? Or do you want to fuck my pussy while I let Sam fuck my ass? Or do you want my ass?"

Dean didn't get a word out, just a cut-off cry of desire. Jess huffed a quiet laugh.

"Doesn't matter what you want right now, I'm your dom and what I want matters right now, sweetheart. I'm going to keep sucking you off until you want to come so bad that you beg me to and I'm going to let Sam do whatever he wants to me.” As she said it, she was pulling off her nurse’s costume.

"Jesus, Jess, stop talking," Sam said, coming up behind her and burying a hand in her hair to pull her back to him. He pressed a sloppy kiss to her jawline and nipped at her ear and his hips ground against her backside. She hummed in pleasure at the way his hardened cock dug into her flesh. Sam kept kissing down from her ear onto her neck and tried to suck a bruise onto her shoulder. He bit against the back of her neck and bucked his hips harder. "I want to fuck your ass," he breathed out against her. "Please."

"I said you could do whatever you wanted," Jess moaned back and rolled her hips against him. "I meant it."

Dean's hips were thrusting upward slightly, enough for Jess to notice, but not enough for her to move any quicker to do anything about it.

"Get the lube, please, Sam," Jess said turning her head. She felt Sam nod with a groan and she turned back to grin at Dean. "Because Sam's going to get to fuck my tight ass and you're going to take whatever I give you while that's going on, aren't you, Dean?" Dean nodded, his bottom lip between his teeth and no sense of pride on his face. "Does it make you mad that baby brother gets to do whatever he wants to me and you have to go on my whims? I could make you just lie here and watch and not even touch you, tell you exactly how good it makes me feel to have Sam fuck me that way, and you wouldn't do a thing to stop me at this point would you?"

Dean didn't answer, just continued to rock his hips shallowly back and forth against the bed and nothing, hoping for some friction somehow. Jess slapped a hand down against his chest, her fingertips landing on his nipple. It stung, badly, and he cried out, his hips rising off the bed further. "I asked you a question, Dean. Would you do anything to stop me?"

"No."

"No what?"

"No, ma'am, I wouldn't stop you from telling me how much you like it when my brother fucks your ass."

Jess leaned down and plunged her tongue into Dean's mouth, massaging his. The kiss was sloppy and hot and both of them moaned into it.

"You're such a good sub, Dean," Jess praised. "You make me so wet talking about your brother like that. Even when before you two were always so shy about it."

Sam had repositioned himself behind Jess, throwing a condom onto the bed next to them while one was still in his hand along with the small bottle of lube. He snapped open the bottle and poured some onto his fingers, letting it drip down between the web of them. His fingers slid down Jess' back, following her spine until he hit the crack of her ass and spreading her cheeks gently.

"You ready for this, Jess?" he asked, kissing against her neck again.  Jess bent herself over and scooted back enough that she could comfortable hover with her mouth right above Dean's cock. Then she murmured out an 'mmmhmm.'

One of Sam's lubed fingertips slipped past the ring of muscle and Jess put on a show of biting her lip in pleasure with her eyes locked on Dean's.

A moan escaped Dean's lips at the sight and Jess smirked at him. He threw his head back so he wouldn't have to look at her.

"Oh, no, Dean, you look at me while your brother opens me up. You watch me get fucked," Jess commanded. Dean's eyes snapped back down to hers. "Good."

Sam had slipped his finger deeper and Jess groaned at that too. Another fingertip teased at her rim, and Jess wiggled backwards, trying to get Sam to do something. He leaned over and kissed her shoulder, trailing his mouth across her back as he slipped the other finger in, just as deep as the first. He thrust, slowly, almost gently, and Jess could feel every minute movement so sharply.

"Fuck, Sam, please," she gasped out.

Sam's other hand left her hip to slide around in front of her and find her clit. He ran his fingers up her slick folds to tease and then circled her clit, making her whine out. Dean watched all this with pupils dilated and his bottom lip between his teeth.

"Are you ready for another one, Jess?" Sam asked just above a whisper. Jess nodded. She cried out at Sam's third finger, and he made calming noises and stroked at her clit more. He moved his fingers, shallowly, and he kept his other hand moving steadily. Jess' breath was quick and sweat beaded up on her forehead. "Are you okay?"

"Yes, Sam, yes, I'm good. Please fuck me. Don't stop."

"Fuck," Dean breathed out.

"You like this, Dean?" Jess asked, breathily. "You like knowing Sam's going to fuck my tight little ass and I'm going to love it?"

"Jesus, Jess," Sam groaned, Jess was fucking herself back on his hands now and Sam rubbed against her clit harder. Jess bucked back hard, once and dipped forward, making Sam have to chase her for his fingers not to pop out. He slid them free gently, and Jess whined. She heard him rip open the condom and knew he was fumbling to roll it on.

"Dean, I'm going to blow you. But don't you dare come until I tell you to. And you leave your hands above your head just like they are, alright?"

Dean nodded slightly.

Jess felt the blunt head of Sam's cock against her ass hole and she relaxed as best as she could, eager to feel him inside her. She's always loved doing this with Sam. He was so sweet with her, gentle and caring until she told him not to be and she couldn't wait to feel him inside her while she sucked Dean down, teased him mercilessly. Sam pushed in slowly and Jess felt her eyelids flutter; she felt split open, differently than she had with his fingers, and it felt amazing to her. Then she wrapped her lips around Dean's cock head and the way he cried out in relief shot a bolt of warmth straight through her.

Sam was still rubbing her clit and Jess felt herself throbbing in pleasure. Sam groaned as he bottomed out, hips snug against her. Jess moaned around Dean and felt his thigh muscles twitch under her hands. She bobbed her head down lower, taking more of him in and then Sam began to move. Slowly, bumping his hips against her ass more, and sliding them back away at a painstaking pace. He pulled back enough that jess' rim clung to the head of him before he pushed back in at the same speed. Jess swallowed down Dean's cock until her nose was against his pelvis and gagged a little. She pulled off to breathe as Sam's hips hit her again.

"Fuck me for real, Sam," she gasped out.

He pulled back out and slammed into her, making her cry out a 'yes' before she sucked Dean back into her mouth.

It felt so good to have them both, Sam fucking in an out of her and swallowing around Dean, hearing him trying to hold back groans. Sam's hand once again moved from her hip, where he'd placed it for better leverage, to her sex.

He circled her clit, rubbing on time with his thrusts and god, it felt good, but Jess wanted more. She pulled off Dean, the pop of it lost in his whine and she straightened up, Sam immediately wrapping an arm around her waist. The angle made Jess groan and Sam snapped his hips faster. She reached behind her and tilted her head so Sam could lean and kiss her. Dean whined again as he watched Sam  plunge his tongue into Jess' mouth; the taste of Dean must have been overwhelming.

Jess broke off the kiss.

"I want you both to fuck me."

Sam stilled his hips, but his grip around her waist got tighter.

"What?" Dean asked, not sure he had heard her quite right.

"I want you both to fuck me at the same time," Jess repeated. Her gaze went from Sam's to Dean's and she looked nearly strung out, but serious in her desire. "I want Sam to keep fucking my ass and I want you to fuck my pussy, Dean."

"Oh, fuck," Sam breathed against Jess' hair.

"Will you two do that?" Jess asked, voice shaking a little with arousal. Sam was nodded, his hips moving again, just shallowly, circling around. "Dean?" He nodded and Jess grinned, pushing her hips back into Sam. He groaned quietly.

Jess ripped open the extra condom Sam had gotten out and she slipped it onto Dean, teasingly gripping along the length of his shaft as she did.

His hips bucked up and she slapped down against his thighs, making Dean hiss.

"I'm still in charge," she reminded him. "Now, scoot down here. Keep your arms above your head though. Legs together."

There was very little grace in Dean's movements, but he got himself lower on the bed. There was shuffling as the three of them maneuvered around so they would all be comfortable as they tried to fit together, yet somehow it still seemed sexy, the way the movements brought them all into contact with each other and the way Sam was still inside Jess. Sam and Jess’ legs both bracketed Dean’s, the muscles of all of them moving against each other.

“Are you sure about this?” Sam asked.

Jess didn’t reply, she just gripped Dean’s cock and lowered herself onto it. The sound of their groans filled the room. Jess was keening and Dean was muttering ‘fuck, fuck, fuck’ as she sank down and Sam had to hide his face in Jess’ curls; being able to see the blissed-out look on Dean’s face was too much as he could feel his cock sliding into Jess through her walls. She felt so tight that Sam’s hips rocked forward on their own, harder than he would have liked.

“Oh, Christ, Sam,” Dean gasped out.  His hands balled into fists in the cuffs. Jess slammed a hand down against Dean’s chest and he moaned again.

“Don’t stop, Sam, please don’t stop,” Jess whined. “Please, fuck me down onto your brother’s cock.”

Sam couldn’t have stopped from moving if he’d wanted to at that. His hips snapped back and forth and Jess bounced shallowly, egging on his movements and changing the angle of the way Dean and Sam could feel each other. Jess leaned forward, baring the expanse of her back to Sam, and he followed her so he could lick the line of sweat that was glistening between her shoulder blades before he straightened up and thrust into her harder. Jess hands gripped Dean’s wrists, her nails digging into him and she bit at the cord of muscle in his neck.

“C’mon, Dean, fuck me,” she nearly growled at him. He hadn’t been moving, and then he was, rocking his hips up as best he could. He and Sam were off rhythm and Jess, caught between their thrusts, was overwhelmed by sensation at every moment. She felt herself nearing orgasm, the stretch of her body around Sam and Dean’s cocks paired with the way her clit kept grinding down onto Dean with every thrust by either one of them was going to set her off in no time. She felt her inner muscles seizing up and her fingers dug into Dean’s pecs and her hips went wild between the two Winchesters. Her mouth opened in a drawn out groan. It turned into a scream when Sam reached a hand around her and circled her swollen, sensitive clit. His hand brushed against Dean’s pubic hair and Dean bucked up. Jess’ second orgasm crashed over her, her scream turning into a cry, and her knees locking around Dean’s hips. He cried out underneath her and Sam was still thrusting behind her.

Jess’ muscles gripped him, tightening around his cock and Sam felt his orgasm rushing through him. He shoved his hips into Jess’ backside as he spilled into the condom.

“Fuck, Jess, I’m gonna‒” Dean started to blurt out, but Jess shoved her hand over his mouth, forcing two of her fingers into it. Dean sucked down onto them and Jess smirked, still riding her aftershocks.

“I told you not to come until I said you could, Dean.” She pulled her fingers free and trailed them down to one of his nipples. Her other hand came up to the other one. She teased at them. “Ask me.”

“Can I come?” Jess slapped down against one of his nipples lightly. Dean’s voice was gravel. “Please? Please can I come?”

Jess pinched Dean’s nipples and his hips rocketed upwards and when Jess said “come,” Dean did like a shot.  

Sam slipped out of Jess, gently pulling back but making her groan any way. He flopped down onto his back next to his brother as Jess got off of him.

“Holy shit,” Dean breathed out.

“Yeah,” Sam agreed. His chest rose and fell as he gulped down air. He hadn’t expected any of this to happen, at least not like this. He also hadn’t expected to feel so good about it.

“Still doesn’t feel that weird though,” Dean admitted quietly. Sam didn’t need to look at him to know that Dean saw him nod back. He heard Dean fumble for something, then the tell-tale sound of handcuffs unlocking.

Jess came back with a damp cloth in her hand and two glasses of water. She raised her eyebrow at the undone cuffs.

“How’d you slip ‘em?”

Dean shrugged a shoulder. Jess smiled back. She came to the side of the bed and laid a gentle kiss on Dean’s forehead and another on his lips.

“You did so good, Dean. Thank you,” she told him. She wiped the cloth against his forehead to mop up some of the sweat and trailed it down his neck and chest too. “I know you said you don’t want to talk about rewards, but is praise alright? Because you did so well. I’m so glad you spoke up.”

“Yeah,” Dean mumbled out. “Praise is alright.”

“Good.”  Jess kissed him again, and then leaned over to kiss Sam as well. She tossed the rag as close to the hamper as she could and crawled into the bed between Sam and Dean. She curled an arm around Sam, but tangled her legs in Dean’s. “French toast in the morning?”

Dean laughed. “Yeah, sure.”

Jess stifled a yawn and burrows deeper into the pillows and Sam’s side. She couldn’t stifle the next yawn and Sam smiled over at her.

“Go to sleep, Jess.”

“Mmkay,” she nodded, her eyes closed. Sam was still smiling at her when she spoke up again, still falling asleep though. “I think next time you two should at least make-out.”

*

Dean did make French toast the next morning, and true to her word, Jess let the two of them go off together. She had no idea where they were going, but they had promised to be back by Monday morning. A homework and crappy TV filled weekend seemed to be on her plate and that’s all that happened to Jess until late Sunday night when Brady came knocking at her door, looking like utter crap.

It wasn’t the first time it’d happened, and Jess had learned a while ago that there was no use asking him what was the matter; she just opened the door wider and let him in and set about making too many bags of microwave popcorn.

They didn’t say a word to each other as Jess sat down next to him and handed him the remote. Something mindless was on the TV but it would make them laugh and Brady seemed in a better mood as the night went on. Jess was nodding off and Brady leaned on her shoulder and she wondered where he had been that he’d smell faintly like rotten eggs, but then she was asleep and had no time to worry about it.

*

She woke up to flames and laughter and a terrible pain in her stomach and then there was nothing.


	4. Chapter 4

“What the fuck was that?” she could hear Sam asking.

“Jesus, Sammy, I don’t know! He was your friend!”

“His eyes were completely black, Dean! And why would this happen right when you show up and drag me back into hunting?”

Sam and Dean were obviously holding themselves back from screaming at each other. Jess could hear them and hear a steady beep. _Hospital sounds,_ she thought hazily. She tried to feign sleep longer, to hear exactly what Sam and Dean were arguing about, but before she could do anything, she started to cough.

“Jess? Oh, God, Jess, are you okay?” Sam was by her side immediately. “How do you feel?”

Worry was written all over Sam’s face, along with fear, and Jess went to lift a hand to the tracks of his tears. Her fingers were bandaged.

“You got burned. It’ll heal, but it’s gonna scar,” Dean told her. Sam looked wracked with guilt.

“What happened?” Jess choked out. It set her off coughing again. “What about Brady?” Sam’s eyes flashed with hatred at the name and Jess was taken aback. “Sam, what the hell is going on?” she demanded, as strongly as her lungs would allow her to.

Sam sighed, lowering his head; he looked back up and ran a hand over his face before gently placing in on Jess’ arm. “There’s a lot to explain, Jess. A lot. And it’s going to sound crazy, but please believe me.”

With another breath, Sam began to tell her a story.

*

“You’re telling me that monsters are real, and you hunt them?” Jess asked, completely incredulous. “You’ve done this your whole life?”

Sam nodded for what must have been the fifth time.

“And you’re going to drop out of school for now to go after this thing that attacked me and find your dad?”

“That was the plan,” Sam admitted.

“You were just going to leave me behind?” Sam sputtered at the accusation; he’d never had to lie like this to Jess and he wasn’t quite sure how to right then.  “Sam, that doesn’t make any sense. You left me alone and this is what happened.”

“But‒”

“No,” Jess coughed. “You’re just going to have to wait until I’m better and take me along.”

Sam marveled at her. He glanced at Dean before turning back to Jess and simply blinking at her. He turned to Dean once again.

“Hey, don’t look at me,” he shrugged. “She’s your girlfriend.” He may have looked relaxed, legs wide and head leaned back against the wall in the uncomfortable hospital room chair, but Sam could see the tension in Dean’s shoulders with the way they were hunched over.

“Jess,” Sam sighed. “There’d be so much for you to learn.”

“So?” Jess said it as though that hadn’t ever entered her mind as an obstacle.

“Get some more rest and we’ll talk about it later, alright?” Sam said eventually. Jess nodded, her eyelids drooping. Sam leaned forward and pressed a kiss to her forehead.

“Why do you two care so much about kissing each other if you grew up hunting monsters though,” Jess slurred out as she was drifting off to sleep.

All Sam and Dean could do was stare at each other.

*

Sam was the one to break and bring it up later that night while in the passenger seat of the impala. They were headed back to the scene of the crime to see if they could find anything. Neither of them had much hope. Clearing his throat, Sam spoke.

“Do you think she has a point?”

Dean glanced over. He didn’t bother to ask ‘about what?’

“That really what you wanna talk about right now, Sam?”

“No, but have you got any idea what we do from here?” He paused for a moment only to be greeted by Dean’s absolute silence. “I don’t want to leave Jess here on her own. But I’m going after Dad and whatever this thing that attacked her and killed Brady is.”

“I know.”

“But we’ve got no idea if Dad is even gonna be where those coordinates are and we’ve got no idea where to even start doing research for this thing and I have no idea what to tell Jess, so‒”

“Sammy, slow down,” Dean interrupted. “You’re gonna get yourself worked up.”

They were quiet for a while again, with Sam’s breathing steadying out as he calmed himself down. The quiet sounds of the radio filled the car.

“I’m just worried about her,” Sam whispered. Dean opened his mouth to respond, but Sam cut him off by straightening his shoulders and saying “So, I want to talk about something else.”

“And you decide renegotiating the idea of this bizarre threeway we’ve had going on is what you want to talk about?” Dean’s eyebrows shot up to his hairline. “Because that’s normal and not at all weird.”

“Of course it’s weird, Dean,” Sam agreed. “But our whole lives are weird. Being with two people I care about seems like the least weird in some ways.” He muttered the last part.

“There’s a difference between being with and, you know, _being with_ , though, Sam. You know that and I know that and even Jess knows that on some level. Plus, it’s been working out alright so far.”

“I know.”

“Besides,” Dean started. “Even if it isn’t weird, do you want change it? I mean…”

Sam flashed back to the image that had popped into his head on Friday night. Want might be too strong of a word.

They’d reached what was left of the apartment and Dean was out of the car before Sam could even think of how to respond. Dean hurried toward the crime scene tape and ducked under it quickly, but didn’t slow down even when he was out of the line of sight from the street.

“What if I did want to change it?” Sam said when he finally caught up to Dean. Dean stilled and inched his head around. Sam’s eyes were level and clear as he looked back. Dean’s brow furrowed a little. He bit his lip before he turned back around.

“Then I guess we’ve got a lot to figure out.”

They didn’t speak as they searched through what was there. As they’d both suspected, there was nothing. All Sam had left was right there and in the hospital.

*

It took Jess only a few hours to convince Sam and Dean that she was going with them. It was mostly accomplished by the fact that as soon as she got out of the hospital, she arranged to drop out of school for the rest of the year. Sam yelled at her and got no response other than “it’s done, Sam.”

There didn’t seem to be a reason to fight it that hard and so the three of them were on the road.

*

Jess was a natural at hand to hand. She shrugged it off with “Took karate as a kid. Too tall for dance,” and proceeded to hit Dean in the face.

Sam couldn’t stop the laugh that bubbled up from his throat and he couldn’t stop the little thrill that zipped through him at the way Dean glared at him with a fat lip; it reminded him too much of the angry look in Dean’s eye every time they’d sparred at that stage when Sam was growing taller and in the midst of puberty to the point where every bit of contact he had with another body felt good. If he really thought about it, maybe this was always where they were going to end up.

“Feel free to jump in whenever you want, Sammy. Not always going to be a one on one fight.” Dean ducked another swing as he said it and lashed out at Jess’ ribs. It was clear he was pulling his punches to some extent, but there was a gleam of fire in both of their eyes still.

“No,” Jess breathed. She kicked out at Dean and he blocked her. “Stay out of it Sam.”

Dean looked like he was going to say something as he made a move to knock Jess down, but he held back when he saw Jess hold up her hands to stop the fight for a moment.

“Stop pulling your punches, Dean. And let’s make this interesting. If you win, we do whatever you want tonight. If I do, we do what I want.”

Dean cocked an eyebrow but nodded after a moment. Jess turned to Sam.

“I need your okay too, you know.”

“I trust you. Of course, Jess,” Sam responded.  Jess smiled and pushed a strand of hair out of her face where it was sticking to her sweaty forehead. She turned back to Dean. He was grinning.

“Alright. Let’s get it on.”

Jess rolled her eyes but snorted out a laugh and attacked. Dean hadn’t listened to her and was still pulling his punches. Jess had no qualms about kicking his ass, even if half-way through the fight she was sure he was losing on purpose.

Losing was how he wound up naked and tied to a chair watching Jess push Sam onto all fours and coating her fingers in lube. The sounds Sam made as Jess pushed those fingers into him slowly burned through Dean like nothing else had. His stomach flipped at the feeling.

Jess had gotten off the bed to go to her bag and left Sam there with one hand stroking his cock; Dean was envious, dying to get some friction somewhere other than where the ropes bit into him, no matter how much that made him tingle as well.

“Oh fuck,” he breathed out as Jess climbed back onto the bed. A leather harness sat snug around her hips, biting into the flesh of her ass. A red dildo was strapped into the front and Jess took it in her hand to run it down the cleft of Sam’s ass. There was a remote in her other hand.

“Jess,” Sam ground out.

“Do you want to get it wet for me, baby? Or do you want me to lube up and fuck you?” She barely gave Sam time to answer. “I think you should give your brother a show and get it wet for me, but it’s your choice.”

Sam straightened up and turned and immediately drove his tongue into Jess’ mouth. His cock rubbed against her red one and he groaned a little. Jess let Sam push her onto her back and take the remote from her hand. He kissed down her body, sucking on her nipples before dipping his tongue into her navel and then wrapping his lips around the head of her plastic dick. His moan as he took it deeper into his mouth had Dean groaning. He’d hit the button the remote and the buzz of the vibrator stuck in front of the harness filled the room under the sounds of moans and Sam gagging around the dildo to get it slicked up. Jess let him set the pace completely, keeping her hands off him and teasing her own nipples. She let him suck her down more, Dean going crazy at the sight of both Jess watching and Sam popping the dildo in and out of the circle of his lips. She finally tugged on Sam’s hair and brought him up to kiss her. His lips were spit slick and shiny and the kiss between him and Jess was filthy. Precome leaked from Dean.

“Do you want to ride my strap, Sam? Or do you want to get back on your hands and knees and let me fuck you how I know you like it?”

Sam nipped at Jess’ bottom lip before he answered her.

“Stay there.”

Jess grinned up at Sam and wrapped her hands around his waist as he settled himself over her. He wrapped one hand around the dildo and braced himself with the other as he sank down slowly. He keened and it turned into a guttural moan as he bottomed out, his ass flush against Jess. Dean didn’t need to be able to see where the red cock entered Sam; he was transfixed on the looks on Sam and Jess’ faces. Sam’s eyes were rolled back in his head and Jess was biting her lip as Sam began to shallowly rock back and forth. Sam’s breathing grew shallower and quicker and Dean was dying to get a fist around his dick.

“Come on, Sam, fuck yourself like you mean it,” Jess said, bringing a hand up to Sam’s cheek. He bent himself in half to kiss Jess and it changed the angle of her entering him. It showed Dean exactly the way his hole clung to the plastic of the dildo and between the sight of it and the sound of the dirty kiss he and Jess were sharing, Dean was groaning. Sam sped himself up until he was practically bouncing on Jess’ strap-on.

“Does it turn you on more to know your big brother is watching? Knowing that he’s desperate to come just from watching you fuck yourself on me, Sam?” Sam groaned and didn’t respond. Jess smirked up at him through her own pleasure. “If you tell me the truth, I’ll let you come.”

“Jess, fuck.”

“Come on, Sam. Do you like that Dean’s watching you get your ass filled? Do you like that he’s watching you getting fucked?”

“Yes,” Sam huffed out.

“What was that?”

“Yes,” Sam said louder. “Yes, I love that Dean’s watching me get my ass drilled. I like that my big brother’s here while I get fucked. Yes, Jess, yes.” Sam was babbling. Jess had sped up her own hips and was snapping them up, hitting Sam’s prostate with every thrust.

“Fuck,” Dean groaned. Neither Jess nor Sam was paying attention to him.

Jess wrapped a hand around Sam’s cock and smeared precome down it with her thumb as she stroked.

“Come for me, baby. Please come on my cock while Dean watches,” Jess ordered. Sam was groaning, long and loud, an as Jess kept stroking, he could feel his balls and his stomach tightening. He was so close. Jess gave one more particularly hard thrust and twisted her wrist and Sam felt his orgasm rush him. He came all over his own stomach with a cry that drowned out Jess’ own orgasm.

Dean was panting, still rock hard and wanting as Sam and Jess came down from their orgasms. Sam slowly rose off the dildo still buried in his ass and pulled a few tissues from the box on the table between the beds to clean himself up; he wouldn’t look directly at Dean.  Jess tilted her head back to look at Dean.

“I’m going to keep this on and blow you and you’re going to come looking right at Sam.”

Dean thought he might come at the statement alone.

Jess made good on her word and crawled the small space between the bed and where Dean was tied. His cock was rock hard and he moaned loudly at Jess’ hand wrapping around the base of his cock.

“Look at Sam,” Jess commanded before Dean’s eyes snapped up to Sam’s and Jess sucked his cock as far down her throat as she could take it.

Dean came while looking right in Sam’s eyes as he was biting his lip at the look on Dean’s face.

Neither Sam nor Dean was willing to discuss how fucked up that was as Jess untied Dean and praised him for how well he’d done. The both of them were fairly certain they were completely fucked, but that moment was not the right time to bring it up. It was the moment to smash onto one bed all together, hear Jess apologize for taking over for the night, and fall asleep.

*

It was another two weeks before the dynamics of their threesome came up. They’d just laid a poltergeist to rest and Dean was coming out of the shower with a towel wrapped around his hips. Jess looked up from the computer where she was doing research.

“I think we need to discuss what happened the last time we were all together.”

Sam and Dean caught each other’s eye. They quickly looked away.

Jess crossed her arms over her chest. “Avoid looking at each other all you want, but the fact of the matter is that you’re both into the other one being there.”

“You’re right, Jess” Sam nodded with a sigh.

“And I know you feel weird about it,” she went on as if he hadn’t said a word. “But you don’t have to on my account. I’m not going to look at you two differently if you want to change how things are happening. I mean, hell,” she smiled, “I’d think it was hot if you did.”

“Oh, we know,” Dean assured her. He was pulling on a pair of boxers and his jeans after that. Jess perhaps should have been embarrassed by his tone, but she wasn’t.

“I’m just saying that it seems like you guys might want to head in that direction,” Jess shrugged.

“Don’t you think we’d bring it up ourselves if we did?” Dean asked, yanking his shirt down over his head and running a hand through his hair to spike it forward. His towel landed in the corner where he threw it. Jess’ eyebrows rose. Sam was shaking his head at his brother.

“Don’t get defensive like that, Dean.” Dean turned his glare on Sam, but Sam just glared back. “You can’t just be this guy who’s along for the ride here with this okay? You have to be honest with us.”

Dean scoffed at that and Sam pursed his lips into a thin white line. He looked about ready to yell but Jess laid a hand on his arm.

“Take off your shirt, Dean,” Jess commanded. Sam turned to look at her with a question in his eyes that echoed the one in Dean’s; Jess reassured him with a smile at him before turning an imperious gaze back on Dean.

Dean hesitated for only a moment before taking his shirt back off. He tossed it back into his bag. Straightening up, he hooked his thumbs into his pockets and waited. At the jerk of Jess’ chin, he laid back on the bed.

Before Jess moved to do anything, she spoke up. “If you don’t want to talk, do you want to do this instead?” At Dean’s nod she went on. “I need you to say it out loud, Dean. Do you want to be my sub right now? Safeword’s Impala like always.”

“Yes, Jess, we can do this right now. I know the damn safeword.”

“Alright, I just wanted to get that cleared up. Now keep quiet until I tell you otherwise.” Jess leaned down and found Dean’s belt in his bag and brought it up, snapping the leather for effect. She then went to Sam’s bag and got his belt as well.

Jess crawled onto the bed and pushed Dean’s arms above his head. She secured them one at a time to the posts in the corners. The muscles in his arms tensed, but he didn’t complain of discomfort; he didn’t say anything at all, actually. He remained silent when Jess straddled his hips and ran her hands up and down his chest.

“Now, Sam, I want you to pay special attention to this session, alright?”

“Okay,” Sam said, uncertainty in his voice. He still needed a shower, but it didn’t seem as though now were the time to bring it up.

“Dean’s not really reacting to the way I’m touching him right now, so I know that teasing isn’t the way to start this off.” Jess took the hem of her shirt in her hands and pulled it off. She reached behind her and unhooked her bra, discarding it on the floor next to the bed, right away. Her breasts hung heavy and she brought her hands up to tease her fingertips around her nipples. She pinched at them and rolled them, darkening them and making them harder, and she rocked her hips. With a moan, she dropped her hands to Dean’s head and leaned down to kiss him, keeping her hips moving.

The kiss was loud. Sam could hear the way Jess’ teeth snapped around Dean’s bottom lip and the way Dean tried to suppress a groan. Jess was smiling as she straightened up.

“That sort of teasing seemed to work. You just have to pay attention to your sub’s likes and dislikes. Now that Dean’s turned on, the other sort of teasing would probably work.” Jess scratched her nails down Dean’s torso to demonstrate. The tendons in Dean’s neck popped out as he tried to keep himself from arching up. “Dean responds more to pain than he wants to let on,” Jess informed him with a conspiratorial smile. Dean gasped as she pinched his nipples, much harder than she had her own. His hips rocketed off the bed when she let go and pinched again without warning. She was still toying with his reddening nipples and she bent down to bite at his neck. Dean groaned.

Jess had moved by the time he thrust his hips up again. His cock was hard and pressing against his zipper and while Jess was off of Dean, Sam found himself thinking about what it would feel like to rock his own hard dick against it. He didn’t try to stop the thought; in fact, he let it guide his hand to his dick so he could palm it through his jeans.  

Something about Jess explaining all of this as though it would be his turn soon made his cock hard in seconds. Jess being topless and Dean looking like he did didn’t hurt either, and Sam wasn’t going to examine any of this too closely; he spent enough time not letting himself go after what he wanted.

Jess had crawled back onto the bed and now she had a half-spent candle from a ritual they’d done a while back and a lighter in her hand. Dean’s brow furrowed as Jess lit the candle and set it on the end table between the beds. He didn’t say anything and she gave an enigmatic smile. She went back to kissing Dean, the two of them moaning into each other’s mouths, but moved so that he could kiss against her neck and shoulders. She’d just moved lower so he could mouth at her breasts when she stuck her hand out and grabbed the lit candle.

“I’m going to drip this wax onto you now, Dean,” she said. She titled the candle and dripped some of the wax onto her own forearm. “It’s hot, but it shouldn’t burn too badly. You know what to do if you don’t like it.”

Dean nodded at the loosely implied question.

Jess ran a hand down the center of Dean’s torso and then tilted the candle so that wax followed the exact trail. Dean hissed at the contact and his stomach muscles twitched, but his hips bucked up hard. The muscles in his arms stood out as he twisted in his restraints.

“You’re doing so good, Dean,” Jess told him. She held the candle out of the way and leaned down to kiss him gently and at the whine Dean gave then, Sam unzipped his jeans to wrap a hand fully around his cock. Jess straightened and poured more wax down the center of Dean’s chest.

Jess was still swiveling her hips against Dean’s erection. She moved her arm so that when she tilted the candle it hit the top of Dean’s chest near his shoulder and the wax cascaded down towards his stomach. Jess kept moving, trails of white wax decorating Dean’s chest, making him whine out.

“See how he’s responding so well? You can see it in his eyes, but you can see the way his muscles are moving, the way he keeps rocking up into me. Those are things you’d want to look out for as a dom, Sam.”

Sam was nodding even though Jess couldn’t see him.

Jess moved the candle and tilted it and grinned as the wax melted down Dean’s chest and hit one nipple. He cried out, loudly, as it did. Jess could feel wetness starting to form through his jeans.

“You’re enjoying this, aren’t you, Dean? Leaking in your pants because it feels so good?” Dean’s nod was desperate. Jess responded by dripping wax onto him the exact way she just had but on his other nipple. Dean looked like he was going to pop a shoulder out of place her arced up so hard at the sensation. Sam’s grip on his cock tightened around the head.

Jess stilled her hips. “I’m going to ask you something now, Dean, and if you’re honest, I’ll give you what you want. Can you do that for me?”

“Yes,” Dean nodded.  

“Do you like that you’re being watched like this?” Jess asked, her voice gentle. Dean nodded, not looking away from Jess’ eyes. She smiled and caressed his ribs. Dean shivered. “Do you mind that it’s Sam watching you?” Dean shook his head ‘no.’ Jess gave him a light stroke again. “Do you like that it’s Sam?” Dean hesitated then, but Jess was still stroking up and down his ribs and her hips were inching back and forth. “You can say no.”

“Yes,” Dean whispered. Jess didn’t make him say it again. Sam choked out a groan. Dean’s eyes flashed toward him.

“Do you want Sam to be more involved? Even a little bit?” Dean’s hesitation was more pronounced then, but Jess’ eyes remained gentle on him as did her hands. He was still hard in his jeans. Dean gave the tiniest nod and Sam let out a sigh of relief. He hadn’t noticed that his breath had caught in his throat.  Jess smiled. “Could he come over here and sit on the bed and keep touching himself?”

Whatever Jess had done to Dean was making him open and honest. He nodded again and Jess turned her smile to Sam. Sam tried not to trip over his own two feet as he made his way to the bed. He sat about even with Jess and kept his hand circled around his dick. Dean kept glancing his way; Sam tried to keep the look on his face gentle, even though the vulnerability in Dean’s eyes was driving him a little wild.

Sam was too used to Dean being fully in control all the time, used to him being angry and ready to fight, and to see him rein that all in hit Sam deep in the gut. It didn’t hurt that Dean looked phenomenal with wax drying all over his chest and Sam couldn’t help but imagining that it was streaks of come. Jess was still rocking her hips, at an almost glacial pace.

“This is one of those sorts of scenes where you probably need to be gentle with your sub. Push too hard and they’ll rebel and safeword out,” Jess told Sam. “You need to know when something should be an order and when it should be a request.”

Sam was about to ask how he’d know, but he scanned Dean’s face and realized that he could read it all over him. Dean wanted this, he really did, but if this was made into anything but a suggestion, he would bail on this whole situation.  Sam was amazed that Jess could read that in his brother so easily as well.

“Dean,” she started. “I want to take your hands out of the belts now, alright? And if you want, I want you to touch Sam. Just his cheek, or his hair, not anything sexual if you don’t want.”

Jess made brisk work of freeing Dean, and Dean’s hands went right to Sam’s hair. His thumbs stoked Sam’s cheeks. Sam closed his eyes and nuzzled into one of Dean’s hands.

“I want you to listen to Sam now,” Jess told Dean. She moved to the chair Sam had occupied. “You two decide what you want to happen.”

Dean nodded and then the moment stretched on forever. Sam wasn’t sure he’d ever seen such gentleness in his brother’s eyes. There were barely any thoughts in Sam’s head. One of Jess’ hands stroked up and down his back and when her nails scratched at him, something snapped in Sam.

“Kiss me,” he told Dean. His tone left room for Dean to refuse, but it conveyed exactly how much Sam didn’t want him to.

Dean surged up and brought his lips to Sam’s. The gentleness that had been in his eyes belied what the kiss was going to be. Dean’s lips on Sam’s were intense, as though if Dean didn’t pour everything into it right away he’d lose his nerve. Sam opened his mouth slightly, gasping at the onslaught, and Dean followed suit. Sam slipped his tongue softly into Dean’s mouth and Dean groaned. Sam deepened the kiss, his softness gaining an edge. It got even harder as Sam wrapped his hands around Dean’s face and plunged his tongue further into Dean’s mouth. Dean whined in the back of his throat and Sam was pushing him down onto his back.

Sam didn’t break the kiss as he threw a leg over Dean’s hip to straddle him and rocked down, bringing his hardness into contact with Dean’s erection. Both of them cried out at the feeling. Sam bit at Dean’s bottom lip and pulled, letting it snap back as he kept grinding his hips. Dean was thrusting his up to match Sam’s rhythm and he groaned out a “Christ, Sammy,” at one emphatic thrust downward.

Dean’s hands carded into Sam’s hair and Sam’s went to Dean’s shoulders, using the leverage to pull Dean closer to him. His fingertips dug into Dean’s muscles, hard, and Dean whined at it. Sam kept rutting down against Dean’s cock and his now tightened stomach muscles. Dean could hardly thrust up because of the angle Sam held him at and he was made even more immobile when Sam maneuvered him to sitting against the headboard. The wood dug into his back and set an ache through him that went right to his cock. When Sam ripped his hands from his hair and pinned them down beside him, another thrill shot through him. For all either of them has hesitated in this, neither of them held back now. Jess’ little hitches of breath egged Dean on further, trying to buck up and groaning when he couldn’t but Sam ground down harder. All they were doing was making out, tongues and teeth and slipping lips, and grinding their cocks against one another but Dean wasn’t sure how long he was going to last.  Sam took one hand from around Dean’s wrist and gripped his own cock through the slit of his boxers, rocking forward and stroking.

Sam threw his head back, breaking the kiss he and Dean had been locked into, and tightened his grip around Dean’s wrist to a painful level. With a twist of his wrist on an upstroke, Sam was coming, sticky and hot on Dean’s stomach. Sam’s hips were still moving, rubbing against Dean’s cock, and paired with Sam’s come splashing onto his abs and the way Sam looked with his mouth wide in a silent cry of pleasure while Dean was trapped under him, Dean was spilling into his jeans.

Sam was up and off Dean in seconds. Instead of looking after him in confusion, Dean turned his eyes on Jess. There was a flush high on her cheeks and a small smile on her lips. She was rocking against her hand unhurriedly. A different sort of pleasure rippled through Dean at the sight.

Sam came back with a warm damp washcloth. His hands were gentle when he brought them to Dean’s stomach and began cleaning him up.

“Sorry about the mess,” he breathed out.  Dean shook his head. They wouldn’t look each other in the eye and Jess noticed. She stilled her hand and made a decision.

“That was sweet and all, but I’m gonna need more than just some frottage, boys.” Sam turned a sharp gaze on her; Dean, a questioning one.

“There’s a name for that?” Sam huffed out a laugh in disbelief.

“You’re kidding me, right?”

Dean’s face contorted into a mask of defense. “What? I don’t need to know the name of something to be able to do it.”

The tension building in the room broke and Jess let out peals of laughter.

Sam was smiling and he moved from Dean’s side, handing the washrag to him, to scoop Jess up off the chair and lay her down on the bed. She was still laughing and Sam undid her pants and scooted them down off her hips.

“Dean,” Sam started, then pressed a kiss right below Jess’ navel. “Get her to stop laughing.”

Dean caught Sam’s eye and knew exactly what he was after.

Jess did stop laughing as Dean kissed her, thorough and sweet, and Sam licked her open until she came.


	5. Chapter 5

“I wasn’t joking about wanting more than just frottage out of you two, you know,” Jess said while Sam and Dean were wedged into the bathroom brushing their teeth. She was toweling off her hair, about to toss the towel in the corner of the bathroom.

Sam paused with his toothbrush in his left cheek. Dean took the chance to spit and elbow Sam out of the way to rinse. He caught Jess’ eye in the mirror.

“What if we said no?”

Jess wore a mild look of surprise for a moment. “Then that’d be fine. I wouldn’t ask you to do something you’re not comfortable with. You know that. I would‒”

“Jess,” Sam cut her off. “We’re not saying no.”

“You’re not?”

“Nah, we talked about it this morning while you were still knocked out,” Dean shrugged and then cheekily smiled at her.

Jess whacked him on the arm and left the crowded bathroom to go get her clothes on. She came back in a pair of ripped up jeans and a white v-neck with a flannel over it and her hair in a ponytail. She still looked like the girl Sam had met at Stanford and fallen in love with over coffee and term papers, except for the burn scar that shone on arm and the hard glint of darkness in the back of her eyes. Somehow, she fit with them better than he had ever imagined she could have.

“So?” she asked with an impatient eyebrow raise.

“So what?” Dean asked.

“So what did you discuss, of course.”

Sam was wiping off his hands and then pushed Dean out of the bathroom. There was no reason for them all to be in that space.  

“We discussed how we’d want it to work,” Sam started, as Dean rolled his eyes. Sam had had to whisper at him very heatedly to get him to talk that morning, but he finally had. Of course, now he didn’t want to act like he’d been part of it. If he wanted to be that way, Sam would just talk about him. “Dean still wants to act as a sub‒”

“Oh, good. I think he’ll so pretty getting fucked‒”

“Whoa, whoa,” Dean stopped her with a hand up. Jess looked taken aback. “Nothin’s going up my ass.”

“There’s no need to get defensive about it, Dean,” Jess pointed out. “Have you ever tried it?”

“Yeah,” Dean said, shocking the hell out of her. Sam had had almost the same reaction that morning. “It’s got nothing to do with it being Sam, it’s just not my thing. Not when there’s other options and he‒” Dean pointed at Sam “is so obviously into it.”

“Wait,” Jess said after a moment. “How exactly do you know it’s not your thing?”

Dean hadn’t explained that part to Sam and he turned bright red when Jess asked. Her eyes lit up like a beacon.  Dean shook his head.

“I’m not drunk enough for this.” Jess whooped out a laugh and Dean stormed across the room to his bag and slung it over his shoulder. “Can we go? There’s a case out near Blue Earth and Jim expected us yesterday.”

He slammed the door on the way out and Jess couldn’t help but still laugh.

“Jim doesn’t expect us there for another day at least,” Sam told her. He started to laugh too. Jess picked up her bag and looped her arm through Sam’s.

“Does that mean we can get him drunk enough to tell us tonight?”

Sam grinned down at her. “It means we can try.”

*

Dean never got drunk enough to tell them how he knew he didn’t like anal, but they got so swamped with cases in the next month that it didn’t seem to matter. The three of them collapsed into the hotel beds aching and exhausted and in varying combinations of bedmates nearly every night. There were dislocated shoulders, broken fingers, cuts in need of stitches and possible concussions throughout that busy month and the first time they had the chance to relax, Jess insisted that they stay at a decent hotel and spend the cash they had left and she won any argument Sam or Dean tried to make.

“It’s not the honeymoon suite and there’s no whirlpool tub, but we could go down to the Jacuzzi,” Jess said when they got to their room. It was on the second floor and that had nearly sealed the deal for Dean, but he saw there was a fire escape on the outside of the building and caved.

“Fuck that, I want to take one of these babies,” Dean shook the unmarked orange bottle of pain pills in his jacket pocket, “and pass out.”

“You might wanna save those for something worse than a sprained ankle, Dean,” Sam pointed out.

“Got a whole stash out in the trunk. That family with the poltergeist a while back? The mom kept bitching about having chronic back pain. She’d been stashing her refills for years.”

“You stole a middle aged woman’s painkillers?” Jess questioned.

Dean shrugged. He popped the top off the bottle and swallowed a pill down. “She had insurance.”

Sam laughed and Jess shot him a look. He tried to stifle the laugh, but Dean had heard it and smiled at him. He proceeded to get his boots off and flop down onto the bed nearest the door.

“Have fun in the hot tub,” he mumbled into the mattress. “Try not to get diseases.”

Jess threw her shirt at his head when she took it off. Dean was too high to care and even past that by the time Jess and Sam had raided the minibar and walked out the door to enjoy their night of luxury.

Dean was half asleep by the time they came back, and they seemed half way to drunk. Dean was still diagonal on his bed but at some point had taken his jeans off and Jess leaned over him with wet hair.

“Dean,” she whispered. He grunted in acknowledgment. “Dean, we’re going to spend all day in bed tomorrow, okay?” He made another sound which made Jess giggle. “We’re just going to fuck all day. You, me, and Sam. All day.”

“mf’kay” Dean muttered.

“Jess, let him sleep.” Sam said, sounding more sober than Jess thought he should. He threw a towel at her and she ran it through her hair. She let the towel she’d wrapped around her fall and let her bra and panties join the pile as well.

Jess crawled under the blankets and smiled at Sam.

“We’ll have to use Dean’s bed tomorrow.”

Sam quirked an eyebrow as he came to bed after discarding his towel and boxers in the bathroom.

“This one’ll have wet sheets.”

Sam laughed at Jess’ grin and kissed her on the forehead as he got into the other side of the bed. He watched as Jess’ eyelids fluttered closed and her breathing evened out in minutes. He’d barely closed his own eyes before he was asleep, the last month of hunts catching up with him.

The sun barely shone through the curtains in the morning and that was how the three of them could tell that they were in a much nicer place than normal. Sam woke up when Jess rolled out of bed and padded over to Dean’s. She crawled onto his bed and knelt down by his ear.

“Wake up, Dean,” she sing-songed. His head popped up off the pillow and one arm reached out toward his bag. He dropped his arm as he realized it was Jess and he raised his head up even more when he realized she was naked. “Turn over.”

Dean followed the order and it was evident that he was hard. Jess brought a hand down to cup him through his boxers and Dean groaned a little. He groaned more when Jess latched onto his neck and started to give him a hickey.

The bed shifted as Sam put his weight down on it and he met Dean’s eyes. The unspoken question passed between them and Dean nodded his assent. Sam leaned down and kissed Dean softly before straightening up with hardened eyes.

“Stop,” Sam said and Jess straightened up and moved her hand away from Dean. “Dean needs to get naked. You should help him, Jess.” Sam caressed Jess’ wrist lightly as he gave the suggestion. She heard the order in it and nodded. She tore Dean’s shirt off his head and yanked his boxers down and he sputtered out in shock. The sputtering turned into a hiss when she ran her nails down his torso before circling his cock with one hand and toying with his balls with the other.

Sam reached out and took Jess’ face between his hands so he could kiss her, tongue into her mouth and pull moans from her throat just from the kiss. It didn’t matter that she tasted like last night’s booze and sleep and he knew he must have as well; the way she’d woken up and immediately been ready to go was sexy as hell. The sounds she was pulling from Dean helped as well.

Sam pulled away and nodded Jess at Dean. She leaned down and kissed him the same way Sam’d kissed her: in control and dirty. It made Dean rock his hips up. Jess took her hands away from him and he whined in his throat. He brought his hands up from where he’d put them above his head to run his thumbs on the underside of Jess’ breasts. She hummed at the feeling but Sam barked out a “no” and he dropped them back to where they were.

To make up for it, one of Jess’ hands slipped over to take Sam’s cock in her fist and she pumped, slowly and teasingly. She broke off from kissing Dean and smiled at Sam before leaning over Dean, positioning herself just so that her breasts leaned up against his hard cock, and took Sam into her mouth. Sam groaned at the sudden heat and his hips bucked up. Jess swallowed him down until she was gagging and got his cock wet. She pulled off him and wrapped her hand around him again, this time squeezing harder and playing in the slickness. Dean was trying to rut up and slide his cock against Jess’ breasts, but he couldn’t.

Sam tapped Jess’ shoulder and she sat up, only for him to lean down and take as much of Dean’s cock into his mouth as he could. Dean yelled and shoved a fist in his mouth.

“I told you to keep your hands above your head, Dean,” Sam said after he’d pulled off so that Dean’s cock was still a mere breath away from his mouth. Dean nodded and threw his hand back above his head. Jess breathed out a laugh at him but he couldn’t be bothered to care because Sam had popped the head of his cock back into his mouth and was sucking. Dean couldn’t look away from the way his brother’s mouth looked hollowed out around his cock or the way he looked tonguing up the length of it when he pulled off.  He sat up and Dean almost whined, but Sam wrapped a hand around his cock where his mouth had been and took one of Jess’ and placed it on top. Dean’s dick was covered by their grips.

“Dean, you’re going to let Jess sit on your face and you’re going to make her come so many times that she screams, alright?”

Dean nodded frantically, his mouth practically watering at the thought. They hadn’t caught enough of a break to really fuck around in what felt like so long. He was suddenly desperate to taste Jess. She leaned down and kissed him for his response.

“And I’m going to get a condom on you and ride your cock.”

“Oh, fuck,” Dean blurted out. Precome dribbled from the tip of him. Sam grinned down at him.

“Good to know you’re so turned on by the idea of your little brother burying your dick in his ass.”

“Jesus Christ, Sam,” Dean huffed out. His hips rolled on the bed. Sam leaned into the space Jess had just occupied, his lips millimeters from Dean’s.

“But I’m not going to let you see it.”

Dean felt like the bed moved under him, his stomach swooped so hard. He wasn’t sure what Sam meant, but his reaction to it was intense. Just the thought that Sam was going to control the situation that much made his hips keep rolling. He did watch Sam and Jess share another filthy kiss and Sam lean over the edge of the bed to reach into one of the bags thrown haphazardly around the room for a condom.

But then Jess was positioning herself so her knees were in his armpits and her toes dug into his forearms and he closed his eyes and inhaled the scent of her, wet and feminine. Dean licked out at her tentatively and Jess ground herself down onto him in encouragement. He practically growled as he laved at her and Jess rocked on his mouth.

Dean was distracted as Sam rolled the condom onto him, but he was hyper aware of Sam’s knees bracketing his hips and the way he ground his ass against him, teasing him at what was to come. He could hear Sam pushing one finger up into himself, hear the slick sounds of the lube mixed with the slick sounds of his own tongue against Jess. Dean thought he might be shaking in anticipation.

Sam didn’t make him wait long. He gripped Dean in one hand and lined him up and started to sink down onto him. Dean cried out against Jess as the head of his cock breached the ring of muscle. Sam breathed out slowly and continued to slide down Dean’s cock until his ass was flush with Dean’s hips.

Dean had stopped licking Jess, too busy breathing through the sensation of absolute heat and tightness around his cock.

“You’d better be eating her out or I’m not going to move at all, Dean,” Sam warned. Dean had no idea where this side of Sam had come from, but he honestly didn’t care at all as long as he would move somehow because if he didn’t, Dean thought he might die.

Jess cried out as Dean went back to licking at her, clit and cunt, and sucking on her labia, and playing her like he’d been aching to do so. She brought her hands up to her nipples to tease while she watched Sam’s eyelids flutter in pleasure as he started to move. He inched himself almost off Dean’s cock before he slammed himself back down and made Dean moan around Jess’ clit.

Sam’s hands were flat on Dean’s stomach as he pushed himself up and down and Jess put hers down to tangle in them. Sam brought one up to his mouth and sucked one of her fingertips into his mouth. Jess surged forward and kissed Sam around her own finger until he let her run her hand through his hair instead. Both of them continued to rock themselves down onto Dean and when Dean used one of Jess’ movements to suck her clit between his lips, Jess seized and came, starting to shake apart between Sam and Dean’s mouths on her. Dean kept licking and sucking at her until one orgasm turned into a second one and he still didn’t stop. He moved to fuck his tongue in and out of her pussy and lap up her wetness.  

When Jess had her faculties back, she reached down and fisted Sam’s cock. She twisted her wrist on the upstroke around his head and slicked the precome he was leaking down his shaft. She matched the rhythm he was riding Dean in and Sam started to pant. He’d angled himself so Dean’s cock hit his prostate every time and between that and the way Jess was stroking him, he thought he might see stars. Jess slowed her hand down and played right at the crown of his cock until she felt him starting to contract and come, splashing against his and Dean’s stomach.

Sam’s hole tightened and spasmed around Dean’s cock and Dean had to bite his lip from screaming as his hips rocketed off the bed trying to bury his dick deeper in the heat of Sam. His orgasm tore out of him and his hands curled into fists and he yelled even though his mouth was still buried in Jess’ sex.

Jess slid off of Dean sideways and leaned against the headboard and Dean could look at his brother seated on his softening cock. Sam had made a mess of both of them and Dean felt his dick twitch at the sight. Sam slipped off of Dean gently and Dean groaned at the loss of contact.  Sam bent down to swallow that groan with a kiss. It turned sloppy when Sam tasted Jess on Dean’s mouth. He licked into Dean’s mouth until the taste was gone and it was just Dean.

“You felt so good, Dean,” Sam whispered to him. Jess leaned down as well and nudged Sam out of the way to kiss him as well.

“So, so good,” Jess agreed. She and Sam sat back and watched Dean’s chest rise and fall. He was staring at the ceiling for a moment before he turned towards them.

“And we’re supposed to do that all day?”

Jess doubled over in laughter and Sam snorted. Dean looked apprehensive.

Jess finally calmed herself down and kissed Dean on the forehead as she slid out of bed.

“I’ll get us some water and then we’ll talk about how we’re spending the next few hours.”

Dean was fairly certain they were going to hurt themselves if the look in Jess’ eye as she sashayed away to the bathroom was any indication, but with the life they lead, it would have been the best possible way to go.  When he told Sam as much, Sam laughed and nodded.

“You’re not wrong.” His smile turned a little softer. “But I think we’ll be okay.”


	6. Epilogue

Jess’ legs were stretched across the backseat as the impala rolled across the back highways of the plains. Every other field they passed had begun to be harvested and Jess wondered if the Midwest would look like a checkerboard from the air; she was glad she was seeing it from her perspective. She’d seen it a lot in the last couple years, but she still wasn’t tired of it.

Dean was tapping along to the Allman Brothers playing softly. He had it turned down only at the request of Jess, who knew that Sam was working his way through an absolutely massive tome that he hoped would shed some light on how to get Dean out of his crossroads deal. Sam could have worked with Dean blasting Metallica, but Jess didn’t see any reason to make him do so. She’d spent two years at Stanford amazed by Sam’s ability to work in any environment‒ and since being on the road she understood it‒ but when they’d gotten their own place, he’d always had quiet classic rock in the background. Jess wanted him to be as un-stressed as he possibly could be for this work and Dean hadn’t argued.

They’d been on the road for almost two hours before Dean broke into the quiet.

“Anything useful, Sammy?”

“Maybe.” He didn’t look up, still skimming the page and flipping to the next one. He sighed when he got to the end of a section and shut the book. “No, there’s nothing useful so far. It’s all the same information we already know.”

Jess had sat up and hooked her chin over the bench seat and when Sam leaned his head back in disappointment, she took the opportunity to lean over and kiss his temple. Dean took a hand off the wheel and patted Sam’s thigh.

“You’re only a couple sections in. We’ve got six months still,” Jess reassured him, bringing a hand to curl around his shoulder. “Besides, we’re doing what we can.”

“And when we’re not, we’re doing our jobs,” Dean pointed out with a glance Sam’s way. He grinned, “Or fucking like porn stars.”

A laugh burst from Sam’s mouth and he tried to stifle it quickly.

Dean continued. “Life’s been alright, Sam. It still is. I’m not mad about a thing.”

“I still think you maybe should be.” His laughter had lightened his mood and he tossed the book on his lap into the seat next to him. Jess smiled, unseen in the back seat. “Go ahead and turn the music up. I’m done for now.”

Dean clapped Sam on the shoulder and turned the volume up. When the opening notes of “Midnight Rider” came to life from the speakers, he rolled the windows down as well. Dean’s loud and half off-key singing was infectious. Jess quickly succumbed and sang along and soon the wind whipped through the car and all three of their voices carried out into the fall sunshine.


End file.
